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

HRID 1928096Notes

Reaction equation

HRID 1928096 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([C:15]3[CH:20]=[CH:19][N:18]=[C:17](Cl)[CH:16]=3)[N:9]=2)=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:28]=[CH:27][C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][N:24]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([C:15]3[CH:20]=[CH:19][N:18]=[C:17]([C:26]4[CH:25]=[N:24][C:23]([NH2:22])=[CH:28][CH:27]=4)[CH:16]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 574687624-(4-Chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-6-methyl-pyrimidine

Product 1

HCID 686916054-[4-(4-Chloro-phenyl)-6-methyl-pyrimidin-2-yl]-[2,3']bipyridinyl-6'-ylamine

Procedure

The title compound was prepared from 4-(4-chloro-phenyl)-2-(2-chloro-pyridin-4-yl)-6-methyl-pyrimidine (example E.45) (0.158 g, 0.5 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.14 g, 0.65 mmol) according to the general procedure VI. Obtained as an off-white solid (0.032 g, 17%). MS (ISP) 374.0 [(M+H)+]; mp 199° C.

Sources & evidence

ORD record
ord-19c25713456a456eb43fcfb4a8a47966
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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