2-Aminopyrimidine-5-boronic acid, pinacol ester → 5-{1-[4-(4-Chloro-phenyl)-6-cyclopropyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-pyrimidin-2-ylamine

HRID 1928040Notes

Reaction equation

HRID 1928040 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[N: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:26]=[N:25][C:24]([NH2:23])=[N:29][CH:28]=4)[N:3]=[CH:4]3)[N:12]=2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 574687382-(4-Bromo-imidazol-1-yl)-4-(4-chloro-phenyl)-6-cyclopropyl-pyrimidine

Product 1

HCID 602093675-{1-[4-(4-Chloro-phenyl)-6-cyclopropyl-pyrimidin-2-yl]-1H-imidazol-4-yl}-pyrimidin-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)pyrimidine (0.18 g, 0.8 mmol) according to the general procedure VI. Obtained as a white solid (0.093 g, 37%). MS (ISP) 390.3 [(M+H)+]; mp 238-240° C.

Sources & evidence

ORD record
ord-a631c989ed46403f8a8b148ce15ab36a
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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