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

HRID 1989315Notes

Reaction equation

HRID 1989315 reaction equation
Br[C:2]1[N:3]=[CH:4][N:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH:10]=[C:9]([CH:20]3[CH2:22][CH2:21]3)[N:8]=2)[CH:6]=1.[NH2:23][C:24]1[CH:29]=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26][N:25]=1>>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[CH:10]=[C:9]([CH:20]3[CH2:22][CH2:21]3)[N:8]=[C:7]([N:5]3[CH:6]=[C:2]([C:27]4[CH:28]=[CH:29][C:24]([NH2:23])=[N:25][CH:26]=4)[N:3]=[CH:4]3)[N:12]=2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 574687382-(4-Bromo-imidazol-1-yl)-4-(4-chloro-phenyl)-6-cyclopropyl-pyrimidine

Product 1

HCID 602093665-{1-[4-(4-Chloro-phenyl)-6-cyclopropyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 2-(4-bromo-imidazol-1-yl)-4-(4-chloro-phenyl)-6-cyclopropyl-pyrimidine (example E.14) (0.30 g, 0.8 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.18 g, 0.8 mmol) according to the general procedure VI. Obtained as an off-white solid (0.08 g, 26%). MS (ISP) 389.3 [(M+H)+]; mp 220-222° C.

Sources & evidence

ORD record
ord-41cad769d2a7410ab16b44e2e5976252
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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