Réaction #6350

Équation de réaction

6-Benzyloxyamino-4-chloro-2,5-diformamidopyrimidine

→

title compound

Rendement 62.0%

9-Benzyloxy-6-chloro-2-formamidopurine

Rendement 62.0%

Solvants

diethoxymethyl acetate

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   Autreevaporated under reduced pressure
3. 3
   Autrethe solvent removed under reduced pressure

Mode opératoire

6-Benzyloxyamino-4-chloro-2,5-diformamidopyrimidine (1.2 g, 3.73 mmol) and diethoxymethyl acetate (20 ml) was stirred at 120° C. for 2.5 hours, cooled and evaporated under reduced pressure. A solution of the residue in methanol (20 ml) and 0.880 ammonia (2 ml) was stirred at 20° C. for 1 hour, the solvent removed under reduced pressure and the residue co-evaporated with methanol. Column chromatography on silica gel (eluted with chloroform-ethanol, 100:1) afforded the title compound (700 mg, 62%). IR: νmax (KBr) 3119, 1702, 1611, 1577, 1505, 1440 cm-1 ; 1H NMR: δH [(CD3)2SO], 5.44 (2H, s, CH2Ph), 7.45 (5H, m, Ph), 8.54 (1H, s, H-8), 9.34 (1H, s, CHO), 11.30 (1H, br.s, D2O exchangeable, NH). Found: C, 49.99; H, 3.37; N, 22.43%, m/z 303.0523. C13H10N5O2Cl+0.5 H2O requires: C, 49.92; H, 3.55; N, 22.40%, m/z 303.0520.

Source