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

HRID 1928114Notes

Reaction equation

HRID 1928114 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[C:17]([CH3:25])[CH:16]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:26][C:27]1[CH:32]=[CH:31][C:30](B2OC(C)(C)C(C)(C)O2)=[CH:29][N:28]=1>>[CH3:14][C:12]1[CH:11]=[C:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[C:17]([CH3:25])[CH:16]=2)[N:9]=[C:8]([C:4]2[CH:3]=[C:2]([C:30]3[CH:31]=[CH:32][C:27]([NH2:26])=[N:28][CH:29]=3)[CH:7]=[CH:6][CH:5]=2)[N:13]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 574687702-(3-Bromo-phenyl)-4-methyl-6-(3-methyl-4-trifluoromethyl-phenyl)-pyrimidine

Product 1

HCID 602094055-{3-[4-Methyl-6-(3-methyl-4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-phenyl}-pyridin-2-ylamine

Procedure

The title compound was prepared from 2-(3-bromo-phenyl)-4-methyl-6-(3-methyl-4-trifluoromethyl-phenyl)-pyrimidine (example E.53) (0.11 g, 0.3 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.087 g, 0.4 mmol) according to the general procedure VI. Obtained as a light brown solid (0.028 g, 22%). MS (ISP) 421.1 [(M+H)+]; mp 153° C.

Sources & evidence

ORD record
ord-51d5ad33369444389d7712bb073de816
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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