N-methyl-2-pyrrolidone → (Tetrahydropyran-4-yl)-thieno[2,3-d]pyrimidin-2-yl-amine

温度

100 °C

A mixture of 2-methanesulfonyl-thieno[2,3-d]pyrimidine (1.58 g, 7.37 mmol), 4-aminotetrahydropyran (2.24 g, 3 eq) and 1-methyl-2-pyrolidinone (2 mL) was heated to 100° C. with stirring for about 7 hours and continued heating at 80° C. overnight. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (180 mL)/water (60 mL). The layers were separated, and the organic layer was washed successively with water (4×60 mL) and brine (1×60 mL). The organic layer was then dried over magnesium sulfate, filtered and concentrated to give 1.7 g of the crude product. Purification by column chromatography on silica gel eluting with 25% ethyl acetate in hexanes afforded the title compound as a white powder (1.264 g) ((M+H)+=236, M.P.=127.0–130.0° C.).

1. temperaturecontinued heating at 80° C. overnight
2. temperatureThe reaction mixture was cooled to room temperature
3. customThe layers were separated
4. washthe organic layer was washed successively with water (4×60 mL) and brine (1×60 mL)
5. dry with materialThe organic layer was then dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customto give 1.7 g of the crude product
9. customPurification by column chromatography on silica gel eluting with 25% ethyl acetate in hexanes

ORDレコード

ord-f0a73307f5ab435fad1e94b298214dad

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07091347B2