[ CAS No. 89793-12-4 ] {[proInfo.proName]}

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2D 3D

Structure of 89793-12-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 89793-12-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 89793-12-4 ]

SDS Specification

Alternatived Products of [ 89793-12-4 ]

Product Details of [ 89793-12-4 ]

CAS No. :	89793-12-4	MDL No. :	MFCD09863164
Formula :	C₇H₇ClN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IEMKQRSOAOPKRJ-UHFFFAOYSA-N
M.W :	186.60	Pubchem ID :	10487815
Synonyms :

Calculated chemistry of [ 89793-12-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	43.13
TPSA :	52.08 ?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) :	-6.39 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	1.48
Log Po/w (WLOGP) :	1.31
Log Po/w (MLOGP) :	0.48
Log Po/w (SILICOS-IT) :	1.68
Consensus Log Po/w :	1.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.1
Solubility :	1.48 mg/ml ; 0.00792 mol/l
Class :	Soluble
Log S (Ali) :	-2.18
Solubility :	1.23 mg/ml ; 0.0066 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.75
Solubility :	0.331 mg/ml ; 0.00177 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.61

Safety of [ 89793-12-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Applications of [ 89793-12-4 ]

Ethyl 2-chloropyrimidine-5-carboxylate (CAS: 89793-12-4) can be used in the preparation of Fimepinostat (CUDC-907) (CAS: 1339928-25-4). Fimepinostat (CUDC-907) has been employed in trials investigating the treatment of lymphoma, solid tumors, breast cancer, multiple myeloma, and NUT midline carcinoma, among others.

Application In Synthesis of [ 89793-12-4 ]

* 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 [ 89793-12-4 ]
Downstream synthetic route of [ 89793-12-4 ]

[ 89793-12-4 ] Synthesis Path-Upstream 1~2

1
[ 89793-12-4 ]
[ 98-80-6 ]
[ 85386-14-7 ]

Yield	Reaction Conditions	Operation in experiment
65%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 100℃;	General procedure: To a solution of and halide in the indicated solvent is added boronic acid or ester, carbonate base, and palladium catalyst at room temperature. After stirring at 100 °C overnight, the mixture is cooled and concentrated.Following Procedure B using ii (500 mg, 2.67 mrnol). dioxane (10 mL), phenylboronic acid (650 mg, 5.36 mmoi), potassium carbonate (1.85 g. 13.4 mmol), and Pd(dppf)C12 (50 mg), then purified by silica gel column chromatography (EA:PE = 1:100 to 1:50) to give 20 as a white solid (400 mg, 65percent yield). (MS: M+Hi 229.1)

Reference： [1] Patent: WO2017/176812, 2017, A1, . Location in patent: Paragraph 0215; 0248

2
[ 89793-12-4 ]
[ 1339928-25-4 ]

Reference： [1] Patent: US9249156, 2016, B2,
[2] Patent: US9249156, 2016, B2,
[3] Patent: WO2018/85342, 2018, A1,
[4] Patent: WO2018/85342, 2018, A1,

[ 89793-12-4 ] Synthesis Path-Downstream 1~4

1
[ 95928-49-7 ]
[ 89793-12-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With N,N-dimethyl-aniline; trichlorophosphate; for 2h;Reflux;	Step d: Ethyl 2-chloropyrimidine-5-carboxylate (Compound R-2-1) A mixture of compound 204 (38.0 g, 153 mmol) and phosphoryl trichloride (300 mL) and N,N-dimethylaniline (3 mL) was heated at reflux for 2 h, cooled to room temperature and concentrated. The residue was quenched carefully with ice-water, adjusted pH to 7-8 with sodium carbonate and extracted with EtOAc. The combined organics were washed with ice-water and brine, dried over Na2SO4, evaporated, and purified by column chromatography (eluted with EtOAc/Hexanes, 10%) to afford compound R-2-1 (15 g, 52%) as a white solid. LCMS: 187 [M+1]+. 1H NMR (400 MHz, CDCl3): delta 1.36 (t, J=7.5 Hz, 3H), 4.39 (q, J=7.5 Hz, 2H), 9.08 (s, 2H).
52%	With N,N-dimethyl-aniline; trichlorophosphate; In N,N-dimethyl-aniline; for 2h;Reflux;	A mixture of compound 204 (38.0 g, 153 mmol) and phosphoryl trichloride (300 mL) and N, N-dimethylaniline (3 mL) was heated at reflux for 2 h, cooled to room temperature and concentrated. The residue was quenched carefully with ice-water, adjusted pH to 7-8 with sodium carbonate and extracted with EtOAc. The combined organics were washed with ice-water and brine, dried over Na2SO4, evaporated, and purified by column chromatography (eluted with EtOAc/Hexanes, 10%) to afford compound R-2-1 (15 g, 52%) as a white solid. LCMS: 187 [M+ljt ?H NMR (400 MHz, CDC13): oe 1.36 (t, J 7.5 Hz, 3H), 4.39 (q, J 7.5 Hz, 2H), 9.08 (s, 2H).
52%	With N,N-dimethyl-aniline; trichlorophosphate; for 2h;Reflux;	A mixture of compound 204 (38.0 g, 153 mmol) and phosphoryl trichloride (300 mL) and N, N-dimethylaniline (3 mL) was heated at reflux for 2 h, cooled to room temperature and concentrated. The residue was quenched carefully with ice-water, adjusted pH to 7-8 with sodium carbonate and extracted with EtOAc. The combined organics were washed with ice-water and brine, dried over Na2SO4, evaporated, and purified by column chromatography (eluted with EtOAc/Hexanes, 10%) to afford compound R-2-1 (15 g, 52%) as a white solid. LCMS: 187 [M+1]+. 1H NMR (400 MHz, CDCl3): delta 1.36 (t, J=7.5 Hz, 3H), 4.39 (q, J=7.5 Hz, 2H), 9.08 (s, 2H).

30%		Step 11d: Ethyl 2-chloropyrimidine-5-carboxylate (Compound 0405) A mixture of 0404 (3.60 g, 21 mmol), phosphorus oxychloride (25 mL), and N,N-dimethylaniline (2.5 mL) was heated to reflux for 1.5 h. After removal of the solvent, ice water (10 mL) was added to the residue. The mixture was added to 2 N NaOH (90 ml), and extracted with EtOAc. After work up the residue was purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 5% v/v) to give product 0405 (1.20 g, 30%): LCMS: 187 [M+1]+, 1H NMR (300 MHz, CDCl3): delta 1.42 (t, J=7.5 Hz, 3H), 4.48 (q, J=7.5 Hz, 2H), 9.15 (s, 2H); 1H NMR (400 MHz, DMSO-d6): delta 1.33 (t, J=6.8 Hz, 3H); 4.37 (q, J=6.8 Hz, 2H), 9.18 (s, 2H).
30%		Step lOd: Ethyl 2-chloropyrimidine-5-carboxylate (Compound 0305)A mixture of compound 0304 (3.60 g, 21 mmol), phosphorus oxychloride ( 25 mL), and N,N-dimethylaniline (2.5 mL) was heated at reflux for 1.5 h. After removal of the solvent, ice water (10 mL) was added to the residue. The mixture was added to 2 N NaOH (90 ml), and extracted with EtOAc. The organic layer was evaporated and purified by column chromatography (ethyl acetate in petroleum ether, 5% v/v) to give compound 0305 (1.20 g, 30%): LCMS: 187 [M+l]+, 1H NMR (300 MHz, CDC13): delta 1.42 (t, J= 7.5 Hz , 3H), 4.48 (q, J= 7.5 Hz, 2H), 9.15 (s, 2H); 1H NMR (400 MHz, DMSO-d6): delta 1.33 (t, J = 6.8 Hz, 3H); 4.37 (q, J= 6.8 Hz, 2H), 9.18 (s, 2H).
30%	With N,N-dimethyl-aniline; trichlorophosphate; for 1.5h;Reflux;	Step 17d: Ethyl 2-chloropyrimidine-5-carboxylate (Compound 0605)A mixture of 0604 (3.60 g, 21 mmol), phosphorus oxychloride (25 mL), and N,N-dimethylaniline (2.5 mL) was heated to reflux for 1.5 h. After removal of the solvent, ice water (10 mL) was added to the residue. The mixture was added to 2 N NaOH (90 ml), and extracted with EtOAc. After work up the residue was purified by column chromatography on silica gel (ethyl acetate in petroleum ether, 5% v/v) to give product 0605 (1.20 g, 30%): LCMS: 187 [M+l]+, 1H NMR (300 MHz, CDC13): delta 1.42 (t, J= 7.5 Hz , 3H), 4.48 (q, J= 7.5 Hz, 2H), 9.15 (s, 2H); 1H NMR (400 MHz, DMSO-d6): delta 1.33 (t, J= 6.8 Hz, 3H); 4.37 (q, J= 6.8 Hz, 2H), 9.18 (s, 2H).
30%	With trichlorophosphate; In N,N-dimethyl-aniline; Petroleum ether; for 1.5h;Reflux;	Step 10d: Ethyl 2-chloropyrimidine-5-carboxylate (Compound 0305)[0216]A mixture of compound 0304 (3.60 g, 21 mmol), phosphorus oxychloride (25 mL), and N,N-dimethylaniline (2.5 mL) was heated at reflux for 1.5 h. After removal of the solvent, ice water (10 mL) was added to the residue. The mixture was added to 2 N NaOH (90 ml), and extracted with EtOAc. The organic layer was evaporated and purified by column chromatography (ethyl acetate in petroleum ether, 5% v/v) to give compound 0305 (1.20 g, 30%): LCMS: 187 [M+1]+, 1H NMR (300 MHz, CDCl3): delta 1.42 (t, J=7.5 Hz, 3H), 4.48 (q, J=7.5 Hz, 2H), 9.15 (s, 2H); 1H NMR (400 MHz, DMSO-d6): delta 1.33 (t, J=6.8 Hz, 3H); 4.37 (q, J=6.8 Hz, 2H), 9.18 (s, 2H).
	With trichlorophosphate; at 117℃; for 2h;Cooling with ice;	Step 4: Ethyl 2-chloropyrimidine-5-carboxylate <strong>[95928-49-7]Ethyl 2-oxo-1,2-dihydropyrimidine-5-carboxylate</strong> (100 g, 0.59 mol) was slurried in POCl3 (600 mL) and cooled in an ice/water bath. The reaction mixture was heated to reflux temperature (oil-bath, T=117 C.) for 2 h. The light-brown colored homogeneous reaction mixture was cooled and the excess of POCl3 was removed by vacuum distillation. The semisolid brown residue was cooled (ice-water bath), toluene (400 mL) and a mixture of water (400 mL) and ice (200 g) were added. The mixture was stirred for 2 h and filtered. The organic phase was separated, dried and concentrated to dryness on a rotary evaporator. The dark yellow residue was purified by flash chromatography (SiO2, heptane/ethyl acetate 9/1) to afford the title compound. 1H NMR (500 MHz, DMSO-d6): delta 9.18 (s, 2H); 4.38 (q, 2H); 1.34 (t, 3H).
1.2 g	With trichlorophosphate; In N,N-dimethyl-formamide; for 1.5h;Reflux;	Compound 0304 (3.60g, 21mmol), phosphorous oxychloride (25 mL), and N, was heated for 1.5 hours under reflux N- mixture of dimethyl aniline (2.5 mL). After removal of the solvent, it was added ice-water (10 mL) to the residue. The mixture was added to 2N NaOH (90ml), and extracted with EtOAc. The organic layer was evaporated and purified by column chromatography (petroleum ether containing ethyl acetate, 5% v / v), compound 0305 (1.20g, 30%) was obtained:

Reference： [1]Patent: US9249156,2016,B2 .Location in patent: Page/Page column 34
[2]Patent: WO2018/85342,2018,A1 .Location in patent: Page/Page column 26; 27; 28
[3]Patent: US2020/78364,2020,A1 .Location in patent: Paragraph 0088; 0092
[4]Patent: US2009/76006,2009,A1 .Location in patent: Page/Page column 31; 40
[5]Patent: WO2011/130628,2011,A1 .Location in patent: Page/Page column 138-139
[6]Patent: WO2009/36016,2009,A1 .Location in patent: Page/Page column 69
[7]Patent: US2013/102595,2013,A1 .Location in patent: Paragraph 0216
[8]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 1504 - 1513
[9]Patent: US2011/152295,2011,A1 .Location in patent: Page/Page column 24
[10]Patent: JP2015/187145,2015,A .Location in patent: Paragraph 0202

2
[ 89793-12-4 ]
[ 1339928-25-4 ]

Reference： [1]Patent: US9249156,2016,B2
[2]Patent: US9249156,2016,B2
[3]Patent: WO2018/85342,2018,A1
[4]Patent: WO2018/85342,2018,A1
[5]Patent: US2020/78364,2020,A1
[6]Patent: US2020/78364,2020,A1

3
[ 89793-12-4 ]
[ 1316215-12-9 ]

Reference： [1]Patent: US2016/355486,2016,A1
[2]Patent: US2016/355486,2016,A1
[3]Patent: WO2016/200919,2016,A1
[4]Patent: WO2016/200919,2016,A1
[5]Patent: US2018/36306,2018,A1
[6]Patent: WO2018/81556,2018,A1
[7]Patent: WO2018/81556,2018,A1
[8]Patent: WO2018/98168,2018,A1
[9]Patent: WO2018/98168,2018,A1
[10]Patent: WO2018/81585,2018,A1
[11]Patent: WO2018/81585,2018,A1
[12]Patent: WO2018/98348,2018,A1
[13]Patent: WO2018/98348,2018,A1
[14]Patent: WO2019/106633,2019,A1

4
[ 56622-54-9 ]
[ 89793-12-4 ]
ethyl 2-[(6-methylpyridin-3-yl)methyl]amino}pyrimidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; for 8h;Reflux;	6-Methyl-3-pyridinemethanamine (1 .0 g, 8.19 mmol) was added to a solution of ethyl 2-chloropyrimidine-5-carboxylate (1 .53 g, 8.19 mmol) and DIPEA (1 .59 g, 12.3 mmol) in 2-propanol (8 mL) and the resulting mixture was heated under reflux for 8 hrs. The cooled mixture was concentrated under reduced pressure and the residue purified by column chromatography on silica gel eluting with EtOAc: Pet. Ether (0: 100 to 30:70) to afford the title compound as a yellow solid, 1 .5 g, 67%. 1H NMR (400 MHz, CDCI3) : delta 1 .37 (t, 3H), 2.55 (s, 3H), 4.35 (q, 2H), 4.67 (d, 2H), 7.12 (d, 1 H), 7.56 (dd, 1 H), 8.45 (d, 1 H). 8.85 (br s, 2H). LCMS m/z =273 [M+H]+

Reference： [1]Patent: WO2018/11681,2018,A1 .Location in patent: Page/Page column 85

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Isomers

Technical Information

? Acyl Group Substitution ? Alkyl Halide Occurrence ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? 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 with Organometallic Reagents ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

Historical Records

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[ 89793-12-4 ]

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P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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. 89793-12-4 ] {[proInfo.proName]}

Quality Control of [ 89793-12-4 ]

Related Doc. of [ 89793-12-4 ]

Product Details of [ 89793-12-4 ]

Calculated chemistry of [ 89793-12-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 89793-12-4 ]

Applications of [ 89793-12-4 ]

Application In Synthesis of [ 89793-12-4 ]

[ 89793-12-4 ] Synthesis Path-Upstream 1~2

[ 89793-12-4 ] Synthesis Path-Downstream 1~4

Technical Information

Related Functional Groups of [ 89793-12-4 ]

Chlorides

Esters

Related Parent Nucleus of [ 89793-12-4 ]

Pyrimidines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 89793-12-4 ]

Related Parent Nucleus of
[ 89793-12-4 ]