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ChemicalBook CAS DataBase List 2-MERCAPTO-5,6-DIMETHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE
38201-64-8

2-MERCAPTO-5,6-DIMETHYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-ONE synthesis

4synthesis methods
361368-64-1 Synthesis
3-Thiophenecarboxylic acid, 2-[(aminothioxomethyl)amino]-4,5-dimethyl-, ethyl ester

361368-64-1
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Yield:38201-64-8 24%

Reaction Conditions:

Stage #1: ethyl 2-(aminothioxomethyl)amino-4,5-dimethyl-3-thiophenecarboxylatewith sodium hydroxide in ethanol at 20; for 0.25 h;Heating / reflux;
Stage #2: with acetic acid in ethanol;water at 20;

Steps:

50

To a suspension of ethyl 4,5-dimethyl-2-thioureidothiophene-3-carboxylate (Example 50a) (37 mg, 0.17 mmol) in dry EtOH (10 mL) was added sodium hydroxide (21 mg, 0.52 mmol). The reaction mixture was then stirred at room temperature for 5 minutes and refluxed for 10 minutes. The reaction mixture was cooled to room temperature, neutralized with 10% AcOH and then concentrated to dryness. The residue was purified by chromatography on silica gel (Gradient 0-50% EtOAc in Hexanes) to give the title compound (8 mg) in 24% yield. 1H NMR (400 MHz, DMSO-d6) δ 2.25 (s, 6H), 12.24 (s, 1H), 13.27 (s, 1H). MS 202 (MH+).

References:

US2008/306053,2008,A1 Location in patent:Page/Page column 67

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