4-Chloro-6-iodothieno(3,2-d)pyrimidine → {1-(4-Chlorobenzyl)-2-[4-(6-iodothieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester

HRID 1192308Notes

Reaction equation

HRID 1192308 reaction equation
Cl[C:2]1[C:3]2[S:10][C:9]([I:11])=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:12]([O:16][C:17](=[O:36])[NH:18][CH:19]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)[C:20](=[O:27])[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)([CH3:15])([CH3:14])[CH3:13]>ClCCCl>[C:12]([O:16][C:17](=[O:36])[NH:18][CH:19]([CH2:28][C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)[C:20]([N:21]1[CH2:26][CH2:25][N:24]([C:2]2[C:3]3[S:10][C:9]([I:11])=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:23][CH2:22]1)=[O:27])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 468355504-Chloro-6-iodothieno(3,2-d)pyrimidineHCID 67538094[1-(4-Chlorobenzyl)-2-oxo-2-piperazin-1-yl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 67538988{1-(4-Chlorobenzyl)-2-[4-(6-iodothieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-chloro-6-iodothieno[3,2-d]pyrimidine (0.22 g, 0.742 mmol) in DCE (5 mL)/TEA (2 mL) was added [1-(4-chlorobenzyl)-2-oxo-2-piperazin-1-yl-ethyl]-carbamic acid tert-butyl ester (25 mg, 0.68 mmol). The mixture was refluxed for 2 hours. The solvent was removed and the residue was subject to chromatography on silica gel to afford the product {1-(4-chlorobenzyl)-2-[4-(6-iodothieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (44 mg, 95%). 1H NMR (CDCl3, 400 Hz) δ 8.47 (s, 1H), 7.64 (s, 1H), 7.27-7.25 (d, J=8.4 Hz, 2H), 7.17-7.15 (d, J=8.0 Hz, 2H), 5.44 (d, J=8.8 Hz, 1H), 4.85-4.81 (m, 1H), 3.86-3.50 (m, 7H), 3.24-3.19 (m, 1H), 2.99-2.97 (d, J=7.2 Hz, 2H), 1.43 (s, 9H). MS (ESI+) [M+H]+ 628.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-ba4f89e5dd23458f8bc5da7f11e2e647
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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