Thionyl Chloride → 4-Chloro-5-ethyl-6-methylthieno[2,3-d]pyrimidine

A mixture of 5-ethyl-6-methyl-3-hydrothiopheno[2,3-d]pyrimidin-4-one (0.5 g), thionyl chloride (5 mL) and catalytic amount of DMF (0.2 mL) was refluxed for 1 h. Solvents were removed under vacuum and the mixture was diluted with ice cold water and stirred for 10 min. The solution was extracted with chloroform (3×100 mL) and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was triturated with hexane to give the product as a dark brown color solid (400 mg, 73%), mp 52-56° C. 1H NMR (400 MHz, CDCl3): δ 8.73 (1H, s), 3.05 (2H, q, J=7.5 Hz), 2.55 (3H, s), 1.24 (3H, t, J=7.6 Hz).

1. temperaturewas refluxed for 1 h
2. customSolvents were removed under vacuum
3. additionthe mixture was diluted with ice cold water
4. extractionThe solution was extracted with chloroform (3×100 mL)
5. washthe combined chloroform layer was washed with water, brine
6. dry with materialdried over sodium sulfate
7. filtrationThe solution was filtered
8. customevaporated the solvent
9. customThe residue was triturated with hexane

ORD record

ord-01577730153149adb1ab8b937889355d

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08815879B2