Réaction #521834

Équation de réaction

N,N-Dimethylformamide dineopentyl acetal

5-chloropyrimidin-2-one

3-furanmethanol

→

pyrimidinone

5-Chloro-1-(3-furylmethyl)pyrimidin-2-one

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   AutreAfter 11/4 h the reaction mixture was evaporated to dryness
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate (200 ml)
3. 3
   Lavagethe solution washed with water (3×50 ml)
4. 4
   Séchagedried (MgSO4)
5. 5
   Concentrationconcentrated to ca 15 ml by which time crystallisation
6. 6
   TempératureThe suspension was cooled
7. 7
   Autrethe crystals collected
8. 8
   Autrerecrystallised from ethyl acetate

Mode opératoire

N,N-Dimethylformamide dineopentyl acetal (1.8 ml) was added to a stirred mixture of 5-chloropyrimidin-2-one (522 mg) and 3-furanmethanol (0.48 ml) in dry N,N-dimethylformamide (10 ml) under nitrogen and the mixture was then heated at 90° C. After 11/4 h the reaction mixture was evaporated to dryness and then the residue was dissolved in ethyl acetate (200 ml) and the solution washed with water (3×50 ml), dried (MgSO4) and concentrated to ca 15 ml by which time crystallisation had occurred. The suspension was cooled and then the crystals collected and recrystallised from ethyl acetate to give white crystals of the title pyrimidinone (288 mg), m.p. 161.5°-162° C., λmax (EtOH) 333 nm (ε 2,340), λinf 245 nm (ε 4,000).

Source