3,4-Dichlorobenzeneboronic acid → 4-[5-(3,4-Dichlorophenyl)pyrimidin-2-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 393727Notes

Reaction equation

HRID 393727 reaction equation
C(OC(N1CCN(C2N=CC(C3C=CC(F)=CC=3)=CN=2)CC1)=O)(C)(C)C.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][N:37]([C:40]2[N:45]=[CH:44][C:43](Br)=[CH:42][N:41]=2)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].[Cl:47][C:48]1[CH:49]=[C:50](B(O)O)[CH:51]=[CH:52][C:53]=1[Cl:54]>>[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][N:37]([C:40]2[N:45]=[CH:44][C:43]([C:51]3[CH:50]=[CH:49][C:48]([Cl:47])=[C:53]([Cl:54])[CH:52]=3)=[CH:42][N:41]=2)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 3

HCID 27343303,4-Dichlorobenzeneboronic 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 698949894-[5-(3,4-Dichlorophenyl)pyrimidin-2-yl]piperazine-1-carboxylic acid tert-butyl esterYield 78%

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 3,4-dichlorobenzeneboronic acid (0.61 g), to yield the title compound as a white solid (0.93 g, 78%).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-affb49eec5644845ad3e55d479d56e0c
Source dataset
uspto-grants-2004_10
Patent number
US06809100B2

Reaction notes

Loading…