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

HRID 9771

Reaktionsgleichung

CS([C:5]1[N:6]=[CH:7][C:8]2[CH:13]=[CH:12][S:11][C:9]=2[N:10]=1)(=O)=O.[NH2:14][CH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.CN1CCCC1=O>C(OCC)(=O)C.O>[O:18]1[CH2:19][CH2:20][CH:15]([NH:14][C:5]2[N:6]=[CH:7][C:8]3[CH:13]=[CH:12][S:11][C:9]=3[N:10]=2)[CH2:16][CH2:17]1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

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.).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-f0a73307f5ab435fad1e94b298214dad
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091347B2

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