Reacción #6349

Ecuación de reacción

4,6-dichloro-2,5-diformamido-pyrimidine

benzyloxyamine

triethylamine

→

title compound

Rendimiento 46.1%

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

Rendimiento 46.1%

Disolventes

dioxan

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe cooled reaction mixture
2. 2
   Filtraciónwas filtered
3. 3
   Otrothe precipitate collected
4. 4
   Lavadowashed with dioxan (2×5 ml)
5. 5
   Otroevaporated to a syrup

Procedimiento

A mixture of 4,6-dichloro-2,5-diformamido-pyrimidine (1.9 g, 8.09 mmol), benzyloxyamine (1 g, 8.13 mmol), triethylamine (2 ml) and dioxan (20 ml) was stirred at 100° C. for 1 hour. The cooled reaction mixture was filtered and the precipitate collected and washed with dioxan (2×5 ml). The filtrate and washings were combined and evaporated to a syrup. Column chromatography on silica gel (eluted with chloroform-ethanol, 30:1) afforded the title compound (1.2 g, 46%). IR: νmax (KBr) 3242, 1694, 1588, 1472 cm-1 ; 1H NMR δH [(CD3)2SO], 4.89 (2H, s, OCH2Ph), 7.4 (5H, m, Ph), 8.15 (1H, s, CHO), 9.18, 9.42 (1H, 2×br.s, D2O exchangeable, NH), 9.25 (1H, br.s, CHO), 10.91 (2H, br.s, D2O exchangeable, 2×NH). m/z (FAB+ve ion, thioglycerol) MH+ 322.

Fuente