4-Chlorothieno[3,2-d]pyrimidine → [1-(4-Chlorobenzyl)-2-oxo-2-(4-thieno[3,2-d]pyrimidin-4-yl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 1192296Notes

Reaction equation

HRID 1192296 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[C:9](=[O:16])[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:27]1[C:28]2[S:35][CH:34]=[CH:33][C:29]=2[N:30]=[CH:31][N:32]=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=1)[C:9](=[O:16])[N:10]1[CH2:11][CH2:12][N:13]([C:27]2[C:28]3[S:35][CH:34]=[CH:33][C:29]=3[N:30]=[CH:31][N:32]=2)[CH2:14][CH2:15]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 27358214-Chlorothieno[3,2-d]pyrimidineHCID 67538094[1-(4-Chlorobenzyl)-2-oxo-2-piperazin-1-yl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 67540460[1-(4-Chlorobenzyl)-2-oxo-2-(4-thieno[3,2-d]pyrimidin-4-yl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl esterYield 86.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The solution of [1-(4-chlorobenzyl)-2-oxo-2-piperazin-1-yl-ethyl]-carbamic acid tert-butyl ester (60 mg, 0.163 mmol) and 4-Chlorothieno[3,2-d]pyrimidine 950 mg, 0.293 mmol) in Toluene (5 mL)/TEA (1 mL) was refluxed for 12 hours. After the solvent was removed, the residue was subject to chromatography on silica gel to afford [1-(4-chlorobenzyl)-2-oxo-2-(4-thieno[3,2-d]pyrimidin-4-yl-piperazin-1-yl)-ethyl]-carbamic acid tert-butyl ester (71 mg, 86.7%). 1H NMR (CDCl3, 400 Hz) δ 8.60 (s, 1H), 7.76 (d, J=5.2 Hz, 1H), 7.45 (d, J=5.2 Hz, 1H), 7.26 (d, J=8.4 Hz, 1H), 7.15 (d, J=8.4 Hz, 1H), 5.39 (d, J=8.8 Hz, 1H), 4.88-4.82 (m, 1H), 3.94-3.76 (m, 4H), 3.69-3.58 (m, 3H), 3.25-3.22 (m, 1H), 2.98 (d, J=7.2 Hz, 2H), 1.43 (s, 9H). MS (ESI+) [M+H]+ 503.

Workup

  1. customAfter the solvent was removed

Sources & evidence

ORD record
ord-38c24b260faf492d9e754448c61afa58
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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