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

HRID 1928032Notes

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]([CH3:20])[N:8]=2)[CH:6]=1.[NH2:21][C:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][N:23]=1>>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[CH:10]=[C:9]([CH3:20])[N:8]=[C:7]([N:5]3[CH:6]=[C:2]([C:25]4[CH:26]=[CH:27][C:22]([NH2:21])=[N:23][CH:24]=4)[N:3]=[CH:4]3)[N:12]=2)=[CH:14][CH:15]=1

Participants

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

HCID 574687362-(4-Bromo-imidazol-1-yl)-4-(4-chloro-phenyl)-6-methyl-pyrimidine

Product 1

HCID 602093625-{1-[4-(4-Chloro-phenyl)-6-methyl-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-methyl-pyrimidine (example E.12) (0.14 g, 0.4 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.088 g, 0.4 mmol) according to the general procedure VI. Obtained as a light yellow solid (0.045 g, 31%). MS (ISP) 363.1 [(M+H)+]; mp 206-208° C.

Sources & evidence

ORD record: ord-2792e13c012549d5aa6307e4cd15c098
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183262B2

Reaction notes

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