4-(Trifluoromethyl)phenylboronic acid → 4-[5-(4-Trifluoromethylphenyl)pyrimidin-2-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 393731Notes

Reaction equation

HRID 393731 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(OC(N1CCN(C2N=CC(Br)=CN=2)CC1)=O)(C)(C)C.[F:47][C:48]([F:59])([F:58])C1C=CC(B(O)O)=CC=1>>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:48]([F:59])([F:58])[F:47])=[CH:22][CH:21]=3)=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 27343894-(Trifluoromethyl)phenylboronic 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 698948094-[5-(4-Trifluoromethylphenyl)pyrimidin-2-yl]piperazine-1-carboxylic acid tert-butyl esterYield 95%

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 (0.346 g) and 4-(trifluoromethyl)benzeneboronic acid (0.211 g), to yield the title compound as a grey solid (0.392 g, 95%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5335c99af6884d2a86ba1a01fc444d67
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

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