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

HRID 1928130Notes

Reaction equation

HRID 1928130 reaction equation
Br[C:2]1[N:3]=[C:4]([CH3:24])[N:5]([C:7]2[N:12]=[C:11]([CH3:13])[CH:10]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[N:8]=2)[CH:6]=1.[NH2:25][C:26]1[CH:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][N:27]=1>>[CH3:24][C:4]1[N:5]([C:7]2[N:12]=[C:11]([CH3:13])[CH:10]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[N:8]=2)[CH:6]=[C:2]([C:29]2[CH:30]=[CH:31][C:26]([NH2:25])=[N:27][CH:28]=2)[N:3]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 57468778HCID 57468778, compound

Product 1

HCID 602094175-{2-Methyl-1-[4-methyl-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-methyl-6-(4-trifluoromethyl-phenyl)-pyrimidine (example E.64) (0.2 g, 0.5 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.14 g, 0.65 mmol) according to the general procedure VI. Obtained as a light yellow solid (0.11 g, 55%). MS (ISP) 411.0 [(M+H)+]; mp 227.5° C.

Sources & evidence

ORD record
ord-27cc82f5e1b348729baa8d2c043f45f4
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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