2-Aminopyrimidine-5-boronic acid, pinacol ester → 5-{2-[6-Methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-thiazol-4-yl}-pyrimidin-2-ylamine

HRID 1989538Notes

Reaction equation

HRID 1989538 reaction equation
Br[C:2]1[N:3]=[C:4]([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH:10]=[C:9]([CH3:23])[N:8]=2)[S:5][CH:6]=1.[NH2:24][C:25]1[N:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][N:26]=1>>[CH3:23][C:9]1[N:8]=[C:7]([C:4]2[S:5][CH:6]=[C:2]([C:28]3[CH:27]=[N:26][C:25]([NH2:24])=[N:30][CH:29]=3)[N:3]=2)[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[CH:10]=1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 574687942-(4-Bromo-thiazol-2-yl)-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 247604325-{2-[6-Methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-thiazol-4-yl}-pyrimidin-2-ylamine

Procedure

The title compound was prepared from 2-(4-bromo-thiazol-2-yl)-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridine (example E.80) (0.20 g, 0.50 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (0.133 g, 0.60 mmol) according to the general procedure VI. Obtained as a white solid (0.100 g, 48%/o). MS (ISP) 414.2 [(M+H)+]; mp>250° C.

Workup

  1. customObtained as a white solid (0.100 g, 48%/o)

Sources & evidence

ORD record
ord-8f5b320d168a4b6dbcb673097ec137ab
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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