tert-Butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylate → 1-(2-Chloro-3,6-difluorobenzyl)-7-[2-(piperazin-1-yl)pyrimidin-5-yl]-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine

HRID 80540Notes

Reaction equation

HRID 80540 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]3[C:18]([F:19])=[CH:17][CH:16]=[C:15]([F:20])[C:14]=3[Cl:21])[CH2:9][CH2:10][NH:11][C:5]2=[N:4][CH:3]=1.C([N:29]1[CH2:34][CH2:33][N:32]([C:35]2[N:40]=[CH:39][C:38](B3OC(C)(C)C(C)(C)O3)=[CH:37][N:36]=2)[CH2:31][CH2:30]1)(OC(C)(C)C)=O>>[Cl:21][C:14]1[C:15]([F:20])=[CH:16][CH:17]=[C:18]([F:19])[C:13]=1[CH2:12][N:8]1[C:6]2=[N:7][C:2]([C:38]3[CH:37]=[N:36][C:35]([N:32]4[CH2:33][CH2:34][NH:29][CH2:30][CH2:31]4)=[N:40][CH:39]=3)=[CH:3][N:4]=[C:5]2[NH:11][CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 46739020tert-Butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-yl)piperazine-1-carboxylateHCID 866594227-Bromo-1-(2-chloro-3,6-difluorobenzyl)-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine

Product 1

HCID 670078461-(2-Chloro-3,6-difluorobenzyl)-7-[2-(piperazin-1-yl)pyrimidin-5-yl]-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine

Procedure

The entitled compound was prepared from 7-bromo-1-(2-chloro-3,6-difluorobenzyl)-1,2,3,4-tetrahydropyrazino[2,3-b]pyrazine and 2-(4-Boc-piperazin-1-yl)pyrimidine-5-boronic acid pinacol ester using Suzuki coupling conditions as described in Example 1. The Suzuki coupling yielded the desired compound in its BOC protected form. The BOC protected intermediate was then treated with TFA in CH2Cl2 and purified by Silica gel column chromatography.

Sources & evidence

ORD record
ord-2282be6cc86d441fa3e1351186d8ea5c
Source dataset
uspto-grants-2014_09
Patent number
US08846664B2

Reaction notes

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