Sodium hydride → 1-(3,3-Diethoxypropyl)tetrahydropyrimidin-2-one

To a stirred and ice-cooled solution of 3-aminopropionaldehyde diethylacetal (5.88 g, 40 mmole) in diethyl ether (35 mL) was added dropwise 3-chloropropyl isocyanate (4.78 g, 40 mmole). The reaction mixture was stirred at room temperature for 4 hours. The mixture was concentrated and dissolved in N,N-dimethylformamide (40 mL). To this solution was added de-oiled sodium hydride (0.96 g, 40 mmole). The reaction mixture was stirred at 70° C. for 18 hours, concentrated, taken up in diethyl ether (40 mL), and filtered. The filtrate was concentrated and purified by silica gel chromatography, eluting with hexane-ethyl acetate-methanol (10:9.7:0.3), gave 1-(3,3-diethoxypropyl)-tetrahydropyrimidin-2-one (9.05 g) as an oil.

1. stirringThe reaction mixture was stirred at room temperature for 4 hours
2. concentrationThe mixture was concentrated
3. dissolutiondissolved in N,N-dimethylformamide (40 mL)
4. stirringThe reaction mixture was stirred at 70° C. for 18 hours
5. concentrationconcentrated
6. filtrationfiltered
7. concentrationThe filtrate was concentrated
8. custompurified by silica gel chromatography
9. washeluting with hexane-ethyl acetate-methanol (10:9.7:0.3)

ORDレコード

ord-116343ab6f52409da190df2d18211306

出典データセット

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07094778B2