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

HRID 1928279Notes

Reaction equation

HRID 1928279 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])=[C:16]([Cl:21])[CH:15]=3)[CH:11]=[C:10]([CH3:22])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:23][C:24]1[N:29]=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][N:25]=1>>[Cl:21][C:16]1[CH:15]=[C:14]([C:12]2[CH:11]=[C:10]([CH3:22])[N:9]=[C:8]([C:4]3[CH:3]=[C:2]([C:27]4[CH:26]=[N:25][C:24]([NH2:23])=[N:29][CH:28]=4)[CH:7]=[CH:6][CH:5]=3)[CH:13]=2)[CH:19]=[CH:18][C:17]=1[Cl:20]

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 574687992-(3-Bromo-phenyl)-4-(3,4-dichloro-phenyl)-6-methyl-pyridine

Product 1

HCID 602094585-{3-[4-(3,4-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-phenyl}-pyrimidin-2-ylamine

Procedure

The title compound was prepared from 2-(3-bromo-phenyl)-4-(3,4-dichloro-phenyl)-6-methyl-pyridine (example E.85) (0.20 g, 0.509 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (0.124 g, 0.56 mmol) according to the general procedure VI. Obtained as an off-white solid (0.100 g, 48%). MS (ISP) 407.2 [(M+H)+], 409.1 [(M+2+H)+] and 411 [(M+4+H)+]; mp 188° C.

Sources & evidence

ORD record
ord-6a9873487c794c75a6e84f670f4fc8af
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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