1-Benzylpiperazine → (4-Benzyl-piperazin-1-yl)-6-iodothieno[3,2-d]pyrimidine

HRID 1192316Notes

Reaction equation

HRID 1192316 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.[CH2:12]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCCl>[CH2:12]([N:19]1[CH2:24][CH2:23][N:22]([C:6]2[N:7]=[CH:2][C:3]3[S:10][C:9]([I:11])=[CH:8][C:4]=3[N:5]=2)[CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 468355504-Chloro-6-iodothieno(3,2-d)pyrimidine

Product 1

HCID 67540584(4-Benzyl-piperazin-1-yl)-6-iodothieno[3,2-d]pyrimidineYield 88.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-chloro-6-iodothieno[3,2-d]pyrimidine (0.5 g, 1.7 mmol) in DCE (5 mL)/TEA (1 mL) was added 1-Benzyl-piperazine (0.3 g, 1.69 mmol). The mixture was refluxed for 1 hour. The solvent was removed and the residue was subject to chromatography on silica gel to afford (4-Benzyl-piperazin-1-yl)-6-iodothieno[3,2-d]pyrimidine (0.65 g, 88%). 1H NMR (CDCl3, 400 Hz) δ 8.47 (s, 1H) 7.60 (s, 1H), 7.35-7.23 (m, 5H), 3.95-3.92 (m, 4H), 3.51 (s, 2H), 2.59-2.54 (m, 4H). MS (ESI+) [M+H]+ 437.

Workup

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

Sources & evidence

ORD record
ord-b30b93a2f35d408cb760ca402437edcc
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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