Benzylamine → Benzothieno[3,2-d]pyrimidine deriv. 51

HRID 1358276Notes

Reaction equation

HRID 1358276 reaction equation
Cl[C:2]1[C:3]2[S:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC(O)C>[CH2:15]([NH:22][C:2]1[C:3]2[S:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[C:4]=2[N:5]=[CH:6][N:7]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 8218354-Chloro(1)benzothieno(3,2-d)pyrimidine

Product 1

HCID 5328399Benzothieno[3,2-d]pyrimidine deriv. 51Yield 68.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chlorobenzothieno[3,2-d]pyrimidine (111 mg, 0.5 mmol), (see following experimental) and benzylamine (114 mg, 1.0 mmol) (111 mg, 1.1 mmol) in stirred 2-propanol (2 mL) are heated at reflux under N2 for 26 h. The mixture is allowed to cool, and the precipitate is collected by Buchner filtration, rinsed with 2-propanol and water and dried in an oven to give 4-benzylaminobenzothieno[3,2-d]pyrimidine (100 mg, 68%) as a white powder. 1H NMR (DMSO) δ8.60 (1H, s), 8.51 (1H, t, J=5.9 Hz), 8.31 (1H, ddd, J=0.7, 1.4, 8.0 Hz), 8.17 (1H, ddd, J=0.7, 1.8, 8.1 Hz), 7.68 (1H, ddd, J=1.2, 7.0, 8.1 Hz), 7.59 (1H, ddd, J=1., 7.0, 8.1 Hz), 7.36 (2H, d, J=7.4 Hz), 7.33 (2H, t, J=7.3 Hz), 7.24 (1H, t, J 7.2 Hz), 4.79 (2H, d, J=6.0 Hz).

Workup

  1. temperatureat reflux under N2 for 26 h
  2. temperatureto cool
  3. filtrationthe precipitate is collected by Buchner filtration
  4. washrinsed with 2-propanol and water
  5. customdried in an oven

Sources & evidence

ORD record
ord-9159fecb1fb242b68d43bc4eedeae420
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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