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[ CAS No. 17321-93-6 ] {[proInfo.proName]}

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Chemical Structure| 17321-93-6
Chemical Structure| 17321-93-6
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Product Details of [ 17321-93-6 ]

CAS No. :17321-93-6 MDL No. :MFCD00094469
Formula : C5H6BrN3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :LPQVTZJEIXYDQA-UHFFFAOYSA-N
M.W : 188.03 Pubchem ID :18616196
Synonyms :

Calculated chemistry of [ 17321-93-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.1
TPSA : 51.8 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 0.95
Log Po/w (WLOGP) : 1.14
Log Po/w (MLOGP) : 0.51
Log Po/w (SILICOS-IT) : 1.34
Consensus Log Po/w : 1.09

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 : 1.5 mg/ml ; 0.00799 mol/l
Class : Soluble
Log S (Ali) : -1.62
Solubility : 4.46 mg/ml ; 0.0237 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.54
Solubility : 0.549 mg/ml ; 0.00292 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 17321-93-6 ]

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

Application In Synthesis of [ 17321-93-6 ]

* 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 [ 17321-93-6 ]
  • Downstream synthetic route of [ 17321-93-6 ]

[ 17321-93-6 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 108-52-1 ]
  • [ 17321-93-6 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With N-Bromosuccinimide In chloroform for 15 h;
Stage #2: With sodium hydroxide In dichloromethane; chloroform; water		 [0242] To a solution of 4-methylpyrimidine-2-ylamine (10.9 g, lOO mmol) in chloroform (400 mL) was added N-bromosuccinimide (17.8 g, 100 mmol). The solution was stirred in the dark for 15 hours, at which time it was added to CH2Cl2 (140O mL), washed with IN NaOH (3x200 mL) and NaCl(sat.) (100 mL), dried over Na2SO4, filtered and concentrated, yielding 5-bromo-4-methylpyrimidine-2-ylamine (18.8 g, 99percent). LCMS (m/z): 188.0/190.0 (MH+). 1H NMR (CDCl3): δ 8.22 (s, IH), 5.02 (bs, 2H), 2.44 (s, 3H).
91% With N-Bromosuccinimide In chloroform at 20℃; for 2 h; Step 44a: 5-Bromo-4-methylpyrimidin-2-amine (Compound 0601-125)A mixture of 2-amino-4-methylpyrimidine (4.0 g, 36.7 mmol), NBS (7.18 g, 40.3 mmol) in chloroform (100 mL) was stirred for 2 h at room temperature, then the solvent was removed in vacuum. Water (100 mL) was added and stirred for 30 min at room temperature, filtered. The solid was washed with water and dried to get compound 0601- 125 (6.3 g, 91percent) as a white solid. LCMS: 188 [M+l]+, 1H NMR (400 MHz, DMSO-d6) δ 2.32 (s, 3H), 6.79 (s, 2H), 8.21 (s, 1H).
91% With N-Bromosuccinimide In chloroform at 20℃; for 2 h; Step 44a: 5-Bromo-4-methylpyrimidin-2-amine (Compound 0601-125)[0378]A mixture of 2-amino-4-methylpyrimidine (4.0 g, 36.7 mmol), NBS (7.18 g, 40.3 mmol) in chloroform (100 mL) was stirred for 2 h at room temperature, then the solvent was removed in vacuum. Water (100 mL) was added and stirred for 30 min at room temperature, filtered. The solid was washed with water and dried to get compound 0601-125 (6.3 g, 91percent) as a white solid. LCMS: 188 [M+1]+, 1H NMR (400 MHz, DMSO-d6) δ 2.32 (s, 3H), 6.79 (s, 2H), 8.21 (s, 1H).
91% With N-Bromosuccinimide In chloroform at 20℃; for 2 h; Chloroform (100 mL) solution of 2-amino-4-methylpyrimidine (4.0 g, 36.7 mmol), a mixture of NBS (7.18g, 40.3mmol) was stirred at room temperature for 2 hours, then the solvent was removed under vacuum. Water (100 mL) was added and stirred for 30 min at room temperature and filtered. The solid was washed with water, to give the compound 0601-125 and dried as a white solid (6.3g, 91percent).
86% With N-Bromosuccinimide In chloroform for 18 h; Darkness To a solution of 4-methylpyrimidine-2-ylamine (8.0 g, 0.073 mol) in chloroform (320 mL) was added N-bromosuccinimide (13.7 g, 0.077 mol). The reaction mixture was stirred in the dark for 18 hrs. LC/MS indicated the reaction was completed. The mixture was diluted with DCM, then washed with IN NaOH aq solution and brine, dried over MgS04, filtered and concentrated to yield 5-bromo-4-methylpyrimidine-2-ylamin (12 g, Yield: 86percent).
86% With N-Bromosuccinimide In chloroform for 18 h; Darkness To a solution of 4-methylpyrimidine-2-ylamine (8.0 g, 0.073 mol) in chloroform (320 mL) was added N-bromosuccinimide (13.7 g, 0.077 mol). The reaction mixture was stirred in the dark for 18 hrs. LC/MS indicated the reaction was completed. The mixture was diluted with DCM, then washed with 1N NaOH aq solution and brine, dried over MgSO4, filtered and concentrated to yield 5-bromo-4-methylpyrimidine-2-ylamin (12 g, Yield: 86percent).
86% With N-Bromosuccinimide In chloroform for 18 h; Darkness Example 6 4-methyl-5-(4, 4, 5, 5-tetramethyl (1, 3, 2-dioxaborolan-2-yl)) pyrimidine-2-ylamine 42 [0204] To a solution of 4-methylpyrimidine-2-ylamine (8.0 g, 0.073 mol) in chloroform (320 mL) was added N-bromosuccinimide (13.7 g, 0.077 mol). The reaction mixture was stirred in the dark for 18 hrs. LC/MS indicated the reaction was completed. The mixture was diluted with DCM, then washed with IN NaOH aq solution and brine, dried over MgSO4, filtered and concentrated to yield 5-bromo-4-methylpyrimidine-2-ylamin (12 g, Yield: 86percent).
81% With N-Bromosuccinimide In dichloromethane at 25℃; for 16 h; Darkness To a solution of compound 22 (500mg, 4.6 mmol) in DCM (50 mL) was added NBS (820mg, 4.6 mmol). The mixture was stirred in the dark for 16 hours at room temperature. The reaction was quenched with DCM (50 mL) and iN NaOH (50 mL). The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give the title compound 23 as a white solid (700 mg, 81percent yield), which was used directly in the next step without further purification.

Reference： [1] Patent: WO2007/84786, 2007, A1, . Location in patent: Page/Page column 91-92
[2] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 10, p. 774 - 779
[3] Patent: WO2011/130628, 2011, A1, . Location in patent: Page/Page column 180
[4] Patent: US2013/102595, 2013, A1, . Location in patent: Paragraph 0377; 0378
[5] Patent: JP2015/187145, 2015, A, . Location in patent: Paragraph 0330
[6] Patent: WO2012/82997, 2012, A1, . Location in patent: Page/Page column 82
[7] Patent: US2014/65136, 2014, A1, . Location in patent: Paragraph 0197; 0198
[8] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 4, p. 351 - 356
[9] Patent: WO2009/146406, 2009, A1, . Location in patent: Page/Page column 69
[10] Patent: WO2017/219800, 2017, A1, . Location in patent: Paragraph 00184; 00185; 00186
[11] Chemische Berichte, 1930, vol. 63, p. 2601,2607
[12] Patent: US2609372, 1950, ,
[13] Patent: US2609372, 1950, ,
[14] Patent: US2609372, 1950, ,
[15] Patent: US2609372, 1950, ,
[16] Patent: WO2009/13348, 2009, A2, . Location in patent: Page/Page column 64-65
  • 2
  • [ 17321-93-6 ]
  • [ 73183-34-3 ]
  • [ 944401-55-2 ]
YieldReaction ConditionsOperation in experiment
74% With potassium acetate In 1,4-dioxane for 8.33333 h; Inert atmosphere A mixture of 5-bromo-4-methylpyrimidine-2-ylamine (5.0g, 26 mmol), potassium acetate (7.83g, 79.8 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)- 1,3,2- dioxaborolane (7.43 g, 29.2 mmol) in dioxane (140 mL) was stirred for 20 min under nitrogen. 1, 1 '-bis (diphenylphosphino) ferrocene palladium (II) chloride dichloromethane adduct (1.08 g, 1.33 mmol) was added to the reaction mixture. The reaction mixture was heated to 115 °C for 18 h under nitrogen. Upon completion, the mixture was cooled and EtOAc was added. The resulting mixture was sonicated and filtered. Additional EtOAc was used to wash the solid. The combined organic extracts were washed with water, dried over MgS04, filtered and concentrated. The crude was purified by chromatography eluting with 20-100percent EtO Ac/hex ane to yield 4.5 g of 4-methyl-5-(4,4,5,5-tetramethyl (l,3,2-dioxaborolan-2-yl))pyrimidine-2-ylamine (yield: 74percent). 1H-NMR (DMSO, 400 MHz): δ 8.28 (s, 1H), 6.86 (br s, 2H), 2.35 (s, 3 H), 1.25 (s, 12 H). MS (ESI) m/e (M+H+) 236.15, 154.07.
74% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 115℃; for 18 h; Inert atmosphere A mixture of 5-bromo-4-methylpyrimidine-2-ylamine (5.0 g, 26 mmol), potassium acetate (7.83 g, 79.8mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (7.43 g,29.2 mmol) in dioxane (140 mL) was stirred for 20 min under nitrogen. 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride dichloromethane adduct (1.08 g, 1.33 mmol) was added to the reaction mixture. The reaction mixture was heated to 115° C. for 18 h under nitrogen. Upon completion, the mixture was cooled and EtOAc was added. The resulting mixture was sonicated and filtered. Additional EtOAc was used to wash the solid. The combined organic extracts were washed with water, dried over MgSO4, filtered and concentrated. The crude was purified by chromatography eluting with 20~100percent EtOAc/hexane to yield 4.5 g of 4-methyl-5-(4,4,5,5-tetramethyl (1,3,2-dioxaborolan-2-yl))pyrimidine-2-ylamine 26 (yield: 74percent). 1H-NMR (DMSO, 400 MHz): δ 8.28 (s, 1H), 6.86 (br s, 2H), 2.35 (s, 3H), 1.25 (s, 12H). MS (ESI) m/e (M+H+) 236.15, 154.07.
74% With potassium acetate In 1,4-dioxane at 115℃; for 18 h; Inert atmosphere A mixture of 5-bromo-4-methylpyrimidine-2-ylamine (5.Og, 26 mmol ), potassium acetate (7.83g, 79.8 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)- 1,3,2-dioxaborolane (7.43 g, 29.2 mmol) in dioxane (140 mL) was stirred for 20 min under nitrogen. 1, l'-bis (diphenylphosphino) ferrocene palladium (II) chloride dichloromethane adduct (1.08 g, 1.33 mmol) was added to the reaction mixture. The reaction mixture was heated to 115 ° C for 18 h under nitrogen. Upon completion, the mixture was cooled and EtOAc was added. The resulting mixture was sonicated and filtered. Additional EtOAc was used to wash the solid. The combined organic extracts were washed with water, dried over MgSO4, filtered and concentrated. The crude was purified by chromatography eluting with 20-100percent EtOAc/hexane to yield 4.5 g of 42 (yield: 74percent). 1H-NMR (DMSO, <n="71"/>400 MHz): δ 8.28 (s, IH), 6.86 (br s, 2H), 2.35 (s, 3 H), 1.25 (s, 12 H). MS (ESI) m/e (M+H+) 236.15, 154.07.
Reference： [1] Patent: WO2012/82997, 2012, A1, . Location in patent: Page/Page column 83
[2] Patent: US2014/65136, 2014, A1, . Location in patent: Paragraph 0198; 0199
[3] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 4, p. 351 - 356
[4] Patent: WO2009/146406, 2009, A1, . Location in patent: Page/Page column 69-70
[5] Patent: WO2009/13348, 2009, A2, . Location in patent: Page/Page column 67
  • 3
  • [ 17321-93-6 ]
  • [ 73183-34-3 ]
  • [ 108-52-1 ]
  • [ 944401-55-2 ]
Reference： [1] Patent: WO2007/84786, 2007, A1, . Location in patent: Page/Page column 92-93
[2] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 10, p. 774 - 779
[3] Patent: WO2017/219800, 2017, A1, . Location in patent: Paragraph 00187; 00188
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