Sodium Hydroxide → 3-Benzyl-2-propylthieno[3,2-d]pyrimidin-4(3H)-one

HRID 2224093Notes

Reaction equation

[CH2:1]([NH:8][C:9]([C:11]1[S:12][CH:13]=[CH:14][C:15]=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.CCOC(C)=O>[CH2:1]([N:8]1[C:9](=[O:10])[C:11]2[S:12][CH:13]=[CH:14][C:15]=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]=1

Participants

Conditions

Temperature: 135 °C

Procedure

N-Benzyl-3-(butyrylamino)thiophene-2-carboxamide (1-4, 2.00 g, 6.60 mmol) was dissolved in ethylene glycol (15.0 mL) and treated with NaOH pellets (26 mg, 0.66 mmol). The reaction was heated to 135° C. for 3 h and allowed to cool. The reaction was diluted with EtOAc (100 mL) and washed with NH4Cl, H2O (2×20 mL), NaCl (30 mL) and dried with MgSO4. Organics were concentrated to provide 3-benzyl-2-propylthieno[3,2-d]pyrimidin-4(3H)-one (1-5). 1H NMR (300 MHz, CDCl3) δ7.77 (d, J=5.2 Hz, 1H), 7.30 (m, 4H), 7.17 (d, J=6.4 Hz, 2H), 5.43 (s, 2H), 2.73 (m, 2H), 1.85 (m, 2H), 0.98 (t, J=7.3 Hz, 3H); MS 285.0 found 284.3 required.

Workup

temperatureto cool
washwashed with NH4Cl, H2O (2×20 mL), NaCl (30 mL)
dry with materialdried with MgSO4
concentrationOrganics were concentrated

Sources & evidence

ORD record: ord-855e5e616a08496ba9bbdfbc694ad96b
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378411B2

Reaction notes

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