2-Aminopyrimidine-5-boronic acid, pinacol ester → 5-{3-[4-(4-Chloro-phenyl)-6-methyl-pyridin-2-yl]-phenyl}-pyrimidin-2-ylamine

HRID 1928069Notes

Reaction equation

HRID 1928069 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:11]=[C:10]([CH3:21])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:22][C:23]1[N:28]=[CH:27][C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][N:24]=1>>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]2[CH:11]=[C:10]([CH3:21])[N:9]=[C:8]([C:4]3[CH:3]=[C:2]([C:26]4[CH:25]=[N:24][C:23]([NH2:22])=[N:28][CH:27]=4)[CH:7]=[CH:6][CH:5]=3)[CH:13]=2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 574687502-(3-Bromo-phenyl)-4-(4-chloro-phenyl)-6-methylpyridine

Product 1

HCID 602093795-{3-[4-(4-Chloro-phenyl)-6-methyl-pyridin-2-yl]-phenyl}-pyrimidin-2-ylamine

Procedure

The title compound was prepared 2-(3-bromo-phenyl)-4-(4-chloro-phenyl)-6-methyl-pyridine (example E.32) (0.075 g, 0.20 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (0.051 g, 0.2 mmol) according to the general procedure VI. Obtained as a white solid (0.035 g, 45%). MS (ISP) 373.2 [(M+H)+] and 375 [(M+2+H)+]; mp 197-199° C.

Sources & evidence

ORD record
ord-71a06dad752f4947bc0158bbc8ed4496
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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