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

HRID 1928282Notes

Reaction equation

HRID 1928282 reaction equation
Br[C:2]1[S:6][C:5]([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)=[CH:4][CH:3]=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:5]2[S:6][C:2]([C:28]3[CH:27]=[N:26][C:25]([NH2:24])=[N:30][CH:29]=3)=[CH:3][CH:4]=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 574688002-(5-Bromo-thiophen-2-yl)-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridine

Product 1

HCID 247605115-{5-[6-Methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-thiophen-2-yl}-pyrimidin-2-ylamine

Procedure

The title compound was prepared from 2-(5-bromo-thiophen-2-yl)-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridine (example E.86) (0.20 g, 0.502 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (0.124 g, 0.552 mmol) according to the general procedure VI. Obtained as a yellow solid (0.045 g, 21%). MS (ISP) 413.2 [(M+H)+]; mp>250° C.

Sources & evidence

ORD record
ord-c8068f815205479392b2abcbd9ad660e
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

Loading…