5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → 5-{2-Methyl-1-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-1H-imidazol-4-yl}-pyridin-2-ylamine

HRID 1928123Notes

Reaction equation

HRID 1928123 reaction equation
Br[C:2]1[N:3]=[C:4]([CH3:27])[N:5]([C:7]2[N:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[N:8]=2)[CH:6]=1.[NH2:28][C:29]1[CH:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][N:30]=1>>[CH3:27][C:4]1[N:5]([C:7]2[N:12]=[C:11]([C:13]([F:16])([F:14])[F:15])[CH:10]=[C:9]([C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:25])([F:24])[F:26])=[CH:21][CH:22]=3)[N:8]=2)[CH:6]=[C:2]([C:32]2[CH:33]=[CH:34][C:29]([NH2:28])=[N:30][CH:31]=2)[N:3]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 574687742-(4-Bromo-2-methyl-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)pyrimidine

Product 1

HCID 602094125-{2-Methyl-1-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-1H-imidazol-4-yl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 2-(4-bromo-2-methyl-imidazol-1-yl)-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyrimidine (example E.60) (0.23 g, 0.5 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.13 g, 0.6 mmol) according to the general procedure VI. Obtained as a yellow solid (0.11 g, 47%). MS (ISP) 465.3 [(M+H)+]; mp 285° C.

Sources & evidence

ORD record
ord-4d0d733287504c8e916c280038f616ce
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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