Reaction #1833212

Reaction equation

2,6-dichloro-5-methoxy-4-vinyl pyrimidine

dichloromethane methanol

→

title compound

Yield 100.0%

2,6-Dichloro-5-methoxy-pyrimidine-4-carbaldehyde

Yield 100.0%

Conditions

Workup

1. 1
   OtherOzone gas was bubbled
2. 2
   OtherThe reaction was quenched with dimethyl sulfide (50 mL)
3. 3
   Concentrationconcentrated under reduced pressure at 40° C.

Procedure

A solution of 2,6-dichloro-5-methoxy-4-vinyl pyrimidine (50 g, 0.24 mol) in dichloromethane:methanol (4:1, 2 L) was cooled to −78° C. Ozone gas was bubbled therethrough for 5 h. The reaction was quenched with dimethyl sulfide (50 mL). The mixture was slowly warmed to room temperature and concentrated under reduced pressure at 40° C. to provide the title compound (50.5 g, 100%); high-performance liquid chromatography (HPLC; 85% acetonitrile buffered with 0.1% volume per volume (v/v) acetic acid).

Source