2-Aminopyrimidine-5-boronic acid, pinacol ester → 5-[6-Methyl-4-(4-trifluoromethyl-phenyl)-[2,4']bipyridinyl-2'-yl]-pyrimidin-2-ylamine

HRID 1928063Notes

Reaction equation

HRID 1928063 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:11]=[C:10]([CH3:24])[N:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:25][C:26]1[N:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][N:27]=1>>[CH3:24][C:10]1[N:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:29]3[CH:28]=[N:27][C:26]([NH2:25])=[N:31][CH:30]=3)[CH:7]=2)[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:11]=1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 866154422'-Chloro-6-methyl-4-(4-trifluoromethylphenyl)-[2,4']bipyridinyl

Product 1

HCID 247603595-[6-Methyl-4-(4-trifluoromethyl-phenyl)-[2,4']bipyridinyl-2'-yl]-pyrimidin-2-ylamine

Procedure

The title compound was prepared from 2′-chloro-6-methyl-4-(4-trifluoromethyl-phenyl)-[2,4′]bipyridinyl (example E.28) (0.300 g, 0.86 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (0.247 g, 1.26 mmol) according to the general procedure VI. Obtained as a white solid (0.110 g, 31%). MS (ISP) 408.3 [(M+H)+]; mp>245° C.

Sources & evidence

ORD record
ord-5b40ce6778c042b1859cf495a3fc6a75
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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