[ CAS No. 183438-24-6 ] {[proInfo.proName]}

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Quality Control of [ 183438-24-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 183438-24-6 ]

SDS Specification

Alternatived Products of [ 183438-24-6 ]

Product Details of [ 183438-24-6 ]

CAS No. :	183438-24-6	MDL No. :	MFCD01318111
Formula :	C₄H₂BrIN₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	ZEZKXPQIDURFKA-UHFFFAOYSA-N
M.W :	284.88	Pubchem ID :	7006651
Synonyms :

Calculated chemistry of [ 183438-24-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.45
TPSA :	25.78 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.92
Log Po/w (XLOGP3) :	1.58
Log Po/w (WLOGP) :	1.84
Log Po/w (MLOGP) :	1.33
Log Po/w (SILICOS-IT) :	2.71
Consensus Log Po/w :	1.88

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.16
Solubility :	0.199 mg/ml ; 0.000697 mol/l
Class :	Soluble
Log S (Ali) :	-1.73
Solubility :	5.28 mg/ml ; 0.0185 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.45
Solubility :	0.101 mg/ml ; 0.000355 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.03

Safety of [ 183438-24-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 183438-24-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 183438-24-6 ]
Downstream synthetic route of [ 183438-24-6 ]

[ 183438-24-6 ] Synthesis Path-Upstream 1~2

1
[ 183438-24-6 ]
[ 108-95-2 ]
[ 257280-25-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	at 165℃; for 4 h; Inert atmosphere	Step A: Preparation of 5-bromo-2-phenoxypyrimidine A mixture consisting of 5-bromo-2-iodopyrimidine (Bridge Organics, 1.01 g, 3.57 mmol), phenol (Aldrich, 3.35 g, 35.7 mmol), and potassium carbonate (Aldrich, 4.93 g, 35.7 mmol) was stirred neat at 165° C. under a nitrogen atmosphere for four hours. After cooling to room temperature, the mixture was partitioned between ethyl acetate (250 mL) and 1 N hydrochloric acid (4*200 mL). The organic layer was washed with 1 N hydrochloric acid until disappearance of color in the aqueous layer. The phases were separated and the organic phase was washed with water (100 mL) and brine (100 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide an orange oil (1.1 g). The product was purified by flash silica column chromatography. Elution through an 80-g Silicycle.(R). flash silica cartridge with 10percent ethyl acetate in hexanes afforded the title compound as a white solid (0.82 g, 92percent yield); R_f 0.51 with 8:2 v/v hexanes-ethyl acetate; ¹H-NMR (400 MHz; CDCl₃) δ 8.56 (s, 2H), 7.46-7.41 (m, 2H), 7.30-7.24 (m, 1H), 7.20-7.16 (m, 2H); MS (APCI⁺) m/z 252.9 (M+1).
87%	With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 100℃; for 20 h; Inert atmosphere	Procedure: 5-bromo-2-iodopyrimidine (3 mmol), phenol (3.2 mmol), 2-picolinic acid (0.3 mmol), cuprous iodide CuI (0.3 mmol), potassium phosphate (4.5 mmol) was placed in 25 mL dry In a flask, 15 mL of DMSO was added and the mixture was heated to 100° C. under Ar protection. After about 20 hours of reaction, TLC conversion was complete. After the mixture was cooled to room temperature, a large amount of ethyl acetate was added, washed with water four times and extracted twice with ethyl acetate. The EA phases were combined and washed with saturated brine. The organic phase was dried, filtered, evaporated to dryness and purified by silica gel column chromatography to give 1.1 g of a white product. , Yield 87percent

Reference： [1] Patent: US2010/75990, 2010, A1, . Location in patent: Page/Page column 40
[2] Patent: CN108069974, 2018, A, . Location in patent: Paragraph 0194-0196

2
[ 97674-02-7 ]
[ 183438-24-6 ]
[ 1189169-37-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With bis-triphenylphosphine-palladium(II) chloride In toluene at 130℃; for 18 h; Inert atmosphere	5-bromo-2-iodopyrimidine (16 g, 56.16 mmol) and tributyl(l- ethoxyethenyl)stannane (25 g, 69.22 mmol) were dissolved in toluene (500 mL) and purged with N₂for 10 mins. Palladium (2⁺) chloride - triphenylphosphane (1 :2:2) (3.5 g, 4.99 mmol) was added and the reaction mixture was heated at 130 °C for 18 h. The reaction was allowed to cool to r.t. Water (70 ml) and 6M HC1 (280 ml) were added and - -the reaction mixture was allowed to stir vigorously for 4 h. The pH of the mixture was adjusted to pH 7 by the addition of saturated aqueous Na₂C0₃(approximately 300 mL) and the mixture extracted with EtOAc (3 x 350 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (Si0₂, 20-100percent EtOAc in Heptane) to afford the title compound as a golden-yellow solid (7.9 g,70percent). 1H NMR (500 MHz, CDC1₃) δ 8.97 (s, 2H), 2.77 (s, 3H).

Reference： [1] Patent: WO2015/86526, 2015, A1, . Location in patent: Page/Page column 153; 154

[ 183438-24-6 ] Synthesis Path-Downstream 1~6

1
[ 121554-09-4 ]
[ 183438-24-6 ]
[ 442899-45-8 ]

Reference： [1]Chemical Communications,2002,p. 874 - 875

2
[ 183438-24-6 ]
[ 105365-51-3 ]
[ 406461-38-9 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 513 - 516
[2]Patent: US2004/147742,2004,A1 .Location in patent: Page 2

3
[ 183438-24-6 ]
[ 98-80-6 ]
[ 38696-20-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 110℃;Microwave irradiation;	Intermediate 21; <n="54"/>A mixture of 5-bromo-2-iodopyrimidine (1.76 mmol, 0.500 g), phenylboronic acid (1.93 mrnol, 0.235 g), 2M aqueous solution of K2CO3 (4.40 mmo., 2.2 m.), Pd(PPh3J4 (0.18 mmol, 0.203 g) in dioxane (10 ml) was heated at 11O0C overnight in a microwave oven. The solvent was evaporated and the solid residue was extracted between water and ethyl acetate. The organic phase was evaporated and the crude residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate mixtures affording 0.329 g (yield 65percent) of the expected product.ESI/MS (m/e, percent): 235 [(M+1)\\ 100], 237 [(M+1)+, 97].
59%	With tetrakis(triphenylphosphine)palladium (0); In hexane; water; ethyl acetate; toluene;	Step 1: Synthesis of 5-bromo-2-phenylpyrimidine First, 1.97 g of 5-bromo-2-iodopyrimidine, 0.85 g of phenylboronic acid, 7.0 mL of a 2M sodium carbonate aqueous solution, and 18 mL of toluene were put in a 200-mL three-neck flask equipped with a reflux pipe, and the atmosphere in the flask was replaced with nitrogen. After the mixture was degassed by being stirred under reduced pressure, 0.081 g of tetrakis(triphenylphosphine)palladium(0) (abbreviation: Pd(PPh3)4) was added thereto and the mixture was refluxed for 8 hours. Here, 0.040 g of Pd(PPh3)4 was added and the mixture was refluxed for 8 hours, and then, 0.040 g of Pd(PPh3)4 was further added and the mixture was further refluxed for 8 hours to cause a reaction. Water was added to the resulted solution, and an organic layer was extracted with dichloromethane. The obtained solution of the extract was washed with saturated brine, and magnesium sulfate was added for drying. The solution obtained by the drying was filtrated. The solvent of this solution was distilled off, and then the obtained residue was purified by flash column chromatography using hexane and ethyl acetate as a developing solvent in a ratio of 5:1, so that the objective pyrimidine derivative (white powder) was obtained in a yield of 59percent). A synthetic scheme of Step 1 is shown in (b-1) below.
59%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; toluene; for 24h;Inert atmosphere; Reflux;	First of all, 5-bromo-2-iodopyrimidine 1.97g and phenyl boronic acid 0.85g, 2M sodium carbonate aqueous solution 7.0mL, toluene 18mL, reflux condenser put in a 200mL three-necked flask equipped with a, in the flask was replaced with nitrogen. After degassing with stirring under reduced pressure, tetrakis (triphenylphosphine) palladium (0) (abbreviation: Pd (PPh 3 ) 4 ) 0.081 g and the mixture was refluxed for 8 hours. Here, Pd (PPh 3 ) 4 0.040 g was added, and the mixture was refluxed for 8 hours, more Pd (PPh 3 ) 4 0.040 g was added and reacted by refluxing for 8 hours. Water was added to the reaction solution, and the organic layer was extracted with dichloromethane. The resulting extract was washed with saturated brine, and dried over magnesium sulfate. After the drying, the solution was filtered. After evaporating the solvent of this solution, the resulting residue, hexane: ethyl acetate = 5: 1 was purified by flash column chromatography as a developing solvent, to give a pyrimidine derivative of interest (white powder, yield: 59percent).

50%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 42h;Heating / reflux;	Step 1: 5-Bromo-2-phenyl-pyrimidine To a degassed solution of phenylboronic acid (8.93 g, 73.22 mmol, 1.0 equiv; commercially available), 5-bromo-2-iodo-pyrimidine (20.86 g, 73.22 mmol, 1.0 equiv; commercially available) and tetrakis(triphenylphosphine) palladium(0) (0.85 g, 0.73 mmol, 0.01 equiv) in toluene (180 mL) was added Na2CO3 (15.52 g, 146.45 mmol, 2.0 equiv), dissolved in water (60 mL), and the reaction mixture heated to reflux. After 18 h, tetrakis(triphenylphosphine) palladium(0) (0.42 g, 0.37 mmol, 0.005 equiv) was added and the reaction mixture heated for an additional time period of 24 h. The solvent was removed under reduced pressure and the crude reaction product extracted from a sat. solution of NaCl (200 mL) with ethyl acetate (3*150 mL). The combined organic phases were dried over Na2SO4, concentrated by evaporation under reduced pressure and the crude material purified by silica column chromatography eluding with heptane/ethyl acetate (9:1) to provide 8.60 g (50percent) of the title compound.
38%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 115℃; for 16h;Inert atmosphere;	A mixture consisting of 5-bromo-2-iodopyrimidine (Bridge Organics, 10.0 g, 35.1 mmol), benzene boronic acid (Alfa Aesar, 4.25 g, 35.1 mmol), tetrakis(triphenylphosphine)palladium (Strem, 0.405 g, 0.351 mmol), toluene (150 mL), and a 2 M aqueous sodium carbonate solution (35 mL) was stirred at 115° C. (degrees Celsius) under a nitrogen atmosphere for 16 hours. After cooling to room temperature, the mixture was partitioned between chloroform (250 mL) and brine (200 mL). The phases were separated and the organic phase was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an orange oil (9.1 g). The crude product was purified by flash silica column chromatography. Elution through a 500-g Analogix.(R). flash silica cartridge with 100percent hexanes afforded the title intermediate as a white solid (3.15 g, 38percent yield). Rf 0.69 with 9:1 v/v hexanes-ethyl acetate; 1H-NMR (400 MHz; CDCl3) delta 8.83 (s, 2H), 8.44-8.38 (m, 2H), 7.52-7.46 (m, 3H); MS (APCI+) m/z 236.9 (M+1).
35%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; N,N-dimethyl-formamide; at 20 - 80℃; for 2h;Inert atmosphere;	To a stirred solution of compound 361 (1.4 g) in DMF: H20 (4:1, 20 mL) were added sodium carbonate (783 mg, 7.39 mmol) and phenylboronic acid 362 (451 mg, 3.69 mmol), purged under argon for 30 mm. To this was added Pd(PPh3)4 (570 mg, 0.49 mmol) at RT; heated to 80 °C and stirred for 2 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mass was filtered through celite; the filtrate was diluted with water (100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over sodium sulfate, filtered, concentrated in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 2percent EtOAc/ hexanes to afford compound 363 (400 mg, 35percent) as white solid. TLC: 10percent EtOAc/ hexanes (R 0.9); 1H-NMR (DMSO-d6, 400 MHz): oe 8.83 (s, 2H), 8.41-8.39 (m, 2H), 7.50-7.48 (m, 3H).

Reference： [1]Organic Letters,2002,vol. 4,p. 513 - 516
[2]Patent: WO2009/21696,2009,A1 .Location in patent: Page/Page column 52-53
[3]Patent: US2015/349278,2015,A1
[4]Patent: JP2016/6041,2016,A .Location in patent: Paragraph 0250; 0251-0253
[5]Patent: US2008/64697,2008,A1 .Location in patent: Page/Page column 27
[6]Patent: US2010/75990,2010,A1 .Location in patent: Page/Page column 21
[7]Patent: WO2015/138895,2015,A1 .Location in patent: Paragraph 000296

4
[ 121554-09-4 ]
[ 183438-24-6 ]
[ 167018-88-4 ]
[ 155802-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane;	2-(4'-Octyloxyphenyl)-5-bromopyrimidine 8.--Quantities: 5-bromo-2-iodopyrimidine 2 (1.23 g, 4.32 mmol), <strong>[121554-09-4]4-octyloxyphenylboronic acid</strong> 7 (1.33 g, 5.18 mmol), tetrakis(triphenylphosphine)palladium (150 mg, 0.13 mmol), DME (30 ml), aqueous 2M sodium carbonate (30 ml). The experimental procedure was as described for compound 4 to yield the phenylpyrimidine 8 (0.67 g, 43%) (from EtOH), m.p. 95.0 C.; νmax /cm-1 (KBr) 2920, 1605, 1525, 1425, 1260, 1170, 1120 and 790; δ 0.90 (3H, t, Me), 1.20-1.55 (10H, m), 1.84 (2H, quint, OCH2 CH2), 4.02 (2H, t, OCH2), 6.97 (2H, d, J 7, 3'- and 5'-H), 8.33 (2H, d, J 7, 2'- and 6'-H) and 8.76 (2H, s, 4- and 6-H); m/z 366 (M+), 364 (M+), 252 (M+ -C8 H16) 250 (M+ -C8 H16), 195 and 186.

Reference： [1]Patent: US5986096,1999,A

5
[ 37828-58-3 ]
[ 183438-24-6 ]
[ 84539-22-0 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 1715 - 1718

6
[ 1308298-23-8 ]
[ 183438-24-6 ]
[ 183437-80-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 839 - 844

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Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 183438-24-6 ] {[proInfo.proName]}

Quality Control of [ 183438-24-6 ]

Related Doc. of [ 183438-24-6 ]

Product Details of [ 183438-24-6 ]

Calculated chemistry of [ 183438-24-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 183438-24-6 ]

Application In Synthesis of [ 183438-24-6 ]

[ 183438-24-6 ] Synthesis Path-Upstream 1~2

[ 183438-24-6 ] Synthesis Path-Downstream 1~6

Technical Information

Related Functional Groups of [ 183438-24-6 ]

Bromides

Related Parent Nucleus of [ 183438-24-6 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 183438-24-6 ]

Related Parent Nucleus of
[ 183438-24-6 ]