N,N-Diethylaniline → HCID 178434331, compound

A mixture of 3-methyl-7-hydroxypyrazolo[4,3-d]pyrimidine (1.0 g, 6.6 mmol), N,N-diethylaniline (2.0 g) and phosphorous oxychloride (16.5 g) was heated with magnetic stirring in an oil bath. The temperature was raised from 55° to 78° over the course of 40 min. At this point, all of the starting material had dissolved and the solution had turned red. The excess POCl3 was distilled off in vacuo (this procedure took 15 min.) and ice-water (50 ml) was added to the residue. The resulting red solution was saturated with sodium chloride (12 g) whereupon it turned yellow. The solution was extracted with ethyl acetate (4×40 ml) and the combined extract was filtered through alumina (5 g; 80-325 mesh), washed with brine (40 ml), dried (Na2SO4) and evaporated, yielding 0.83 g (74%) of eggshell colored crystals.

1. temperaturewas heated
2. temperatureThe temperature was raised from 55° to 78° over the course of 40 min
3. dissolutionAt this point, all of the starting material had dissolved
4. distillationThe excess POCl3 was distilled off in vacuo (this procedure
5. addition) and ice-water (50 ml) was added to the residue
6. extractionThe solution was extracted with ethyl acetate (4×40 ml)
7. extractionthe combined extract
8. filtrationwas filtered through alumina (5 g; 80-325 mesh)
9. washwashed with brine (40 ml)
10. dry with materialdried (Na2SO4)
11. customevaporated
12. customyielding 0.83 g (74%) of eggshell colored crystals

ORD record

ord-bd471d82b2e1488d8a389b91e2cc7863

Source dataset

uspto-grants-1981_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04282361