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

HRID 1989391Notes

Reaction equation

HRID 1989391 reaction equation
Cl[C:2]1[CH:7]=[C:6]([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:4][N:3]=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:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:30]3[CH:29]=[N:28][C:27]([NH2:26])=[CH:32][CH:31]=3)[CH:7]=2)[N:13]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 574687692-(2-Chloro-pyridin-4-yl)-4-methyl-6-(3-methyl-4-trifluoromethyl-phenyl)-pyrimidine

Product 1

HCID 686925234-[4-Methyl-6-(3-methyl-4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-[2,3']bipyridinyl-6'-ylamine

Procedure

The title compound was prepared from 2-(2-chloro-pyridin-4-yl)-4-methyl-6-(3-methyl-4-trifluoromethyl-phenyl)-pyrimidine (example E.52) (0.11 g, 0.27 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.079 g, 0.36 mmol) according to the general procedure VI. Obtained as a light brown solid (0.021 g, 18%). MS (ISP) 422.1 [(M+H)+]; mp 188° C.

Sources & evidence

ORD record
ord-eee12ce75f924de1be9e0379de47122a
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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