2-Aminopyrimidine-5-boronic acid, pinacol ester → 4-[6-Methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-[2,5']bipyrimidinyl-2'-ylamine

HRID 1989547Notes

Reaction equation

HRID 1989547 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:11]=[C:10]([CH3:24])[N:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:25][C:26]1[N:31]=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28][N:27]=1>>[CH3:24][C:10]1[N:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:29]3[CH:28]=[N:27][C:26]([NH2:25])=[N:31][CH:30]=3)[N:7]=2)[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:11]=1

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 574687972-Chloro-4-[6-methyl-4-(4-trifluoromethylphenyl)-pyridin-2-yl]-pyrimidine

Product 1

HCID 247604364-[6-Methyl-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-[2,5']bipyrimidinyl-2'-ylamine

Procedure

The title compound was prepared from 2-chloro-4-[6-methyl-4-(4-trifluoromethylphenyl)-pyridin-2-yl]-pyrimidine (example E.83) (0.40 g, 1.14 mmol) and commercially available 2-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (0.303 g, 1.37 mmol) according to the general procedure VI. Obtained as a white solid (0.050 g, 10%). MS (ISP) 409.2 [(M+H)+]; mp 264° C.

Sources & evidence

ORD record
ord-0c8a0162f12d493a858167f1c187c2ab
Source dataset
uspto-grants-2010_01
Patent number
US07642264B2

Reaction notes

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