Phosphorus oxychloride → 7-Chloro-2-(Methylsulfanyl)-[1,3]thiazolo[4,5-d]pyriMidine

A mixture of 2-(methylthio)thiazolo[4,5-d]pyrimdin-7-(6H)-one (800 mg) and phosphorous oxychloride (8 mL) was refluxed for 2 h. Solvents were removed under vacuum and the mixture was diluted with chloroform. Again the solvents were removed under vacuum and this procedure repeated twice (yellow color solid). The residue was diluted with ice cold water and basified with 10% aqueous sodium bicarbonate. 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 chromatographed over silica gel column using hexane-ethyl acetate (95:5) as eluents to give the product as a white color solid (750 mg, 86%), mp 148-150° C. 1H NMR (400 MHz, CDCl3): δ 8.95 (1H, s), 2.90 (3H, s); LC-MS (positive ion mode): m/z 218, 220 (M+H)+.

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

ORDレコード

ord-2956da1b6928415fb55bcaedad250e38

出典データセット

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08815879B2