Methyl iodide → (E)-N-Methyl-N-tert-Butyloxycarbonyl-4-(5-pyrimidinyl)-3-butene-1-amine

Under a nitrogen atmosphere, sodium hydride (0.78 g, 19.5 mmol, 60% dispersion in oil) was added to a stirring solution of IV (0.50 g, 2.0 mmol), 1,2-dimethoxyethane (20 mL), DMF (25 mL), and a trace of diisopropylamine. The mixture was stirred at ambient temperature for 45 min, and a solution of iodomethane (2.59 g, 18.3 mmol) in 1,2-dimethoxyethane (5 mL) was added. The mixture was stirred at ambient temperature for 3 days, cooled, and water (25 mL) was added dropwise. The mixture was diluted with water (200 mL) and extracted with chloroform (7×50 mL). All chloroform extracts were combined, dried (Na2 SO4), filtered, and concentrated by rotary evaporation. The residue was dried under high vacuum at ambient temperature to give a red-brown oil, The oil was chromatographed on silica gel (50 g), eluting with ethyl acetate. Selected fractions were combined, concentrated by rotary evaporation, and dried under high vacuum at ambient temperature to give compound V as a light yellow oil (0.40 g, 76.1%).

1. stirringThe mixture was stirred at ambient temperature for 3 days
2. temperaturecooled
3. extractionextracted with chloroform (7×50 mL)
4. customdried (Na2 SO4)
5. filtrationfiltered
6. concentrationconcentrated by rotary evaporation
7. customThe residue was dried under high vacuum at ambient temperature
8. customto give a red-brown oil
9. customThe oil was chromatographed on silica gel (50 g)
10. washeluting with ethyl acetate
11. concentrationconcentrated by rotary evaporation
12. customdried under high vacuum at ambient temperature

ORDレコード

ord-6c4a508ae39645b5b1f65ea3b88e82b8

出典データセット

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05731314