2-Aminopyrimidine-5-boronic acid, pinacol ester → 5-{5-[4-(3,4-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-thiophen-2-yl}-pyrimidin-2-ylamine

HRID 1928284Notes

Reaction equation

HRID 1928284 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=3)[CH:10]=[C:9]([CH3:21])[N:8]=2)=[CH:4][CH:3]=1.[NH2:22][C:23]1[N:28]=[CH:27][C:26](B2OC(C)(C)C(C)(C)O2)=[CH:25][N:24]=1>>[Cl:20][C:15]1[CH:14]=[C:13]([C:11]2[CH:10]=[C:9]([CH3:21])[N:8]=[C:7]([C:5]3[S:6][C:2]([C:26]4[CH:25]=[N:24][C:23]([NH2:22])=[N:28][CH:27]=4)=[CH:3][CH:4]=3)[CH:12]=2)[CH:18]=[CH:17][C:16]=1[Cl:19]

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 574688012-(5-Bromo-thiophen-2-yl)-4-(3,4-dichlorophenyl)-6-methyl-pyridine

Product 1

HCID 247605135-{5-[4-(3,4-Dichloro-phenyl)-6-methyl-pyridin-2-yl]-thiophen-2-yl}-pyrimidin-2-ylamine

Procedure

The title compound was prepared from 2-(5-bromo-thiophen-2-yl)-4-(3,4-dichloro-phenyl)-6-methyl-pyridine (example E.87) (0.25 g, 0.626 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (0.152 g, 0.689 mmol) according to the general procedure VI. Obtained as a yellow solid (0.060 g, 23%). MS (ISP) 413.1 [(M+H)+], 415.2 [(M+2+H)+] and 417 [(M+4+H)+]; mp 237° C.

Sources & evidence

ORD record
ord-44931baa698e4c55ad565df2e8819b69
Source dataset
uspto-grants-2012_05
Patent number
US08183262B2

Reaction notes

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