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GENERAL STEPS: 2,4-Dichlorothieno[3,2-d]pyrimidine (19 g, 58 mmol) was dissolved in a solvent mixture of ethanol (25 mL) and ethyl acetate (25 mL). To this solution was added sodium bicarbonate (1.1 g, 13.1 mmol) followed by 10% palladium carbon catalyst (0.206 g). The reaction mixture was stirred under hydrogen atmosphere for 5 h. The reaction progress was monitored by liquid chromatography-mass spectrometry (LC-MS) to confirm the formation of 2-chlorothieno[3,2-d]pyrimidine. Upon completion of the reaction, the mixture was filtered through diatomaceous earth to remove the catalyst and the filtrate was concentrated under reduced pressure to afford the off-white solid product 2-chlorothieno[3,2-d]pyrimidine (0.990 g, quantitative yield). The structure of the product was confirmed by 1H NMR (CDCl3): δ 9.17 (s, 1H), 8.16-8.12 (d, 1H), 7.55-7.51 (d, 1H).

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