4-Cyanophenylboronic acid → 4-[5-(4-Cyanophenyl)pyrimidin-2-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 393724Notes

Reaction equation

HRID 393724 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[C:32]([N:34]1CCN(C2N=CC(Br)=CN=2)CC1)=O)(C)(C)C.C(C1C=CC(B(O)O)=CC=1)#N>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:32]#[N:34])=[CH:22][CH:21]=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 27343264-Cyanophenylboronic acidHCID 21914476tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylateHCID 69850026Tert-butyl 4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-carboxylate

Product 1

HCID 698940834-[5-(4-Cyanophenyl)pyrimidin-2-yl]piperazine-1-carboxylic acid tert-butyl esterYield 68%

Procedure

Prepared according to the method for the preparation of 4-[5-(4-fluorophenyl)pyrimidin-2-yl]piperazine-1-carboxylic acid tert-butyl ester, from 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylic acid tert-butyl ester (1.00 g) and 4-cyanobenzeneboronic acid (0.47 g), to yield the title compound as a white solid (0.72 g, 68%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ef15a90277444f2fa9bcd11f13edad8f
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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