Diisopropylamine → 5-(3-Hydroxypropylsulfanyl)-3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione

Prepared according to the procedure described in Example 5 from n-butyllithium (2.0M solution in hexanes, 0.32 ml) and diisopropylamine (0.093 ml) in anhydrous tetrahydrofuran (5 ml), 3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.20 g) in anhydrous tetrahydrofuran (5 ml) and 3-{[dimethyl(1,1-dimethylethyl)silyl]oxy}propyl 4-methylphenylthiosulfonate (0.19 g, J. Med. Chem. 1995, 38, 2557) in anhydrous tetrahydrofuran (2 ml). The crude adduct was dissolved in tetrahydrofuran (6 ml) and treated with tetrabutylammonium fluoride hydrate (0.20 g). After 16 hours, the solution was diluted with water (30 ml) and extracted with ether (2×30 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with ether and was then recrystallised from ethyl acetate/hexane to give the title compound (0.098 g).

1. customPrepared
2. extractionextracted with ether (2×30 ml)
3. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
4. filtrationfiltered
5. customevaporated under reduced pressure
6. customThe residue was purified by column chromatography over silica
7. washeluting with ether
8. customwas then recrystallised from ethyl acetate/hexane

ORDレコード

ord-089a131601044cf4b4455581bf54bfcb

出典データセット

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06180635B2