Sodium Hydroxide → 3-Benzyl-2-propylthieno[2,3-d]pyrimidin-4(3H)-one
Reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[NH:16][C:17](=O)[CH2:18][CH2:19][CH3:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)CO>[CH2:1]([N:8]1[C:9](=[O:10])[C:11]2[CH:15]=[CH:14][S:13][C:12]=2[N:16]=[C:17]1[CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A mixture of N-benzyl-2-(butyrylamino)thiophene-3-carboxamide (2-3, 230 mg, 0.76 mmol, 1 equiv) and sodium hydroxide (3 mg, 0.08 mmol, 0.1 equiv) in ethylene glycol (5 mL) was heated at 130° C. for 5 h. The reaction mixture was allowed to cool, then partitioned between a half-saturated aqueous sodium chloride solution and ethyl acetate (2×75 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column (hexanes initially, grading to 100% ethyl acetate) to provide 3-benzyl-2-propylthieno[2,3-d]pyrimidin-4(3H)-one (2-4) as a colorless oil which solidified upon standing. 1H NMR (300 MHz, CDCl3) δ 7.48 (d, 1H, J=5.8 Hz), 7.31 (m, 3H), 7.19 (d, 1H, J=5.8 Hz), 7.17 (d, 2H, J=7.9 Hz), 5.42 (s, 2H), 2.72 (t, 2H, J=7.6 Hz), 1.78 (sextet, 2H, J=7.6 Hz), 0.97 (t, 3H, J=7.3 Hz). 3-benzyl-5,6-dibromo-2-(1-bromopropyl)thieno[2,3-d]pyrimidin-4(3H)-one (2-5) and 3-benzyl-6-bromo-2-(1-bromoyropyl)thieno[2,3-d]pyrimidin-4(3H)-one (2-6)
Workup
- temperatureto cool
- custompartitioned between a half-saturated aqueous sodium chloride solution and ethyl acetate (2×75 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated
- customThe residue was purified by flash column (hexanes initially
Sources & evidence
- ORD record
- ord-72aa3f3c6d2441cf90404fbe9744f4a6
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07378411B2
Reaction notes
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