Isopropanol → 2-Nitroamino-5-(1-benzyl-2-oxo-pyrid-4-ylmethyl)-4-pyrimidone

To a stirred solution of sodium (2.76 g) in methanol (50 ml) was added nitroguanidine (11.10 g. containing 25% water) and methanol (10 ml). The mixture was refluxed for 45 minutes and then ethyl α-formyl-β-(N-benzyl-2-oxo-4-pyridyl)propionate (25.07 g) in methanol (90 ml) was added over one hour. The reaction mixture was refluxed for 24 hours, cooled and evaporated under reduced pressure to afford an oily residue which was dissolved in water (100 ml). The solution was extracted with chloroform (3×50 ml) and the combined chloroform extracts were washed with water (3×25 ml). The combined aqueous layer and aqueous washings were taken to pH 5 with glacial acetic acid to give an oily solid. Isopropanol (35 ml) was added with warming to cause dissolution, on cooling a solid formed which was collected by filtration, washed with water, washed with isopropanol and recrystallised from water-acetic acid to give white crystals of 2-nitroamino-5-(1-benzyl-2-oxopyridin-4-ylmethyl)pyrimidin-4-one (10.40 g), m.p. 200°-201° C.

1. temperatureThe mixture was refluxed for 45 minutes
2. temperatureThe reaction mixture was refluxed for 24 hours
3. temperaturecooled
4. customevaporated under reduced pressure
5. customto afford an oily residue which
6. extractionThe solution was extracted with chloroform (3×50 ml)
7. washthe combined chloroform extracts were washed with water (3×25 ml)
8. customto give an oily solid
9. temperaturewith warming
10. dissolutiondissolution
11. temperatureon cooling a solid
12. customformed which
13. filtrationwas collected by filtration
14. washwashed with water
15. washwashed with isopropanol
16. customrecrystallised from water-acetic acid

ORD record

ord-c6ff1588326147d791226fb82c320be6

Source dataset

uspto-grants-1985_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04540699