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

HRID 1192314Notes

Reaction equation

HRID 1192314 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][CH:8]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[S:25][C:24](I)=[CH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:13][CH2:12]1)=[O:10])([CH3:4])([CH3:3])[CH3:2].[C:36]([Cu])#[N:37]>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:35])[NH:7][CH:8]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:18]3[S:25][C:24]([C:36]#[N:37])=[CH:23][C:19]=3[N:20]=[CH:21][N:22]=2)[CH2:13][CH2:12]1)=[O:10])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

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 esterHCID 178418546HCID 178418546, compound

Product 1

HCID 67539318{1-(4-Chlorobenzyl)-2-[4-(6-cyanothieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl esterYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of {1-(4-chlorobenzyl)-2-[4-(6-iodothieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (50 mg, 0.080 mmol) in Pyridine (5 mL) was added CuCN (20 mg, 0.223 mmol). The mixture was refluxed under N2 for 12 hours. The solvent was removed and the residue was subject to chromatography on silica gel to afford {1-(4-chlorobenzyl)-2-[4-(6-cyanothieno[3,2-d]pyrimidin-4-yl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (29 mg, 69%). 1H NMR (CDCl3, 400 Hz) δ 8.65 (s, 1H), 7.95 (s, 1H), 7.28-7.26 (d, J=7.6 Hz, 2H), 7.18-7.16 (d, J=8.4 Hz, 2H). 5.35-5.33 (d, J=8.4 Hz, 1H), 4.85-4.80 (m, 1H), 3.91-3.56 (m, 7H, 3.24-3.19 (m, 1H), 3.01-2.99 (d, J=8.0 Hz, 2H), 1.44 (s, 9H). MS (ESI+) [M+H]+ 527.

Workup

  1. temperatureThe mixture was refluxed under N2 for 12 hours
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-4f3d1f81f01841caaf8684b9f2d855df
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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