Acetic Anhydride → HCID 135905990, compound

A mixture of 5-amino-4-carbamoyl-3-methylisoxazole (14.9 g), triethylorthoacetate (112 ml) and acetic anhydride (112 ml) was refluxed for seven hours then evaporated in vacuo. The residue was dissolved in 0.880 ammonia solution (250 ml) and the solution treated with charcoal and filtered. The filtrate was acidified to pH 6 with acetic acid and the precipitate filtered and dried to give 3,6-dimethylisoxazolo [5,4-d] pyrimidin-4(5H)-one (9.8 g, m.p. 275°-280°, decomp.). A mixture of this material (3.2 g), thionyl chloride (30 ml) and N,N-dimethylformamide (1 ml) was refluxed for ten minutes, evaporated in vacuo at ca 50°. The residue was dissolved in dichloromethane, washed well with ice-cold water, dried and evaporated to give crude chloro derivative. A solution of this material in acetonitrile (50 ml) was treated with α-methylbenzylamine (4.84 g, two equivalents) keeping the temperature below 15°. The mixture was stirred for twenty hours at room temperature*, evaporated in vacuo, and distributed between ether and water. The extracts were washed, dried, evaporated and distilled in a bulb-tube apparatus (200°-210°/0.05 mm). The distillate crystallised on trituration with petroleum (b.p. 40°-60°). Recrystallisation from cyclohexane gave Compound no 26 of Table I (0.70 g, m.p. 99°-101°).

1. temperaturewas refluxed for seven hours
2. customthen evaporated in vacuo
3. dissolutionThe residue was dissolved in 0.880 ammonia solution (250 ml)
4. additionthe solution treated with charcoal
5. filtrationfiltered
6. filtrationthe precipitate filtered
7. customdried

ORD record

ord-a96f2b35a9414d99b1cfd5fda00acaa2

Source dataset

uspto-grants-1980_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04189483