Dichloromethane methanol → 2,6-Dichloro-5-methoxypyrimidine-4-carbaldehyde

HRID 1468955Notes

Reaction equation

HRID 1468955 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=C)[C:5]([O:10][CH3:11])=[C:4]([Cl:12])[N:3]=1.ClCCl.C[OH:17]>>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=[O:17])[C:5]([O:10][CH3:11])=[C:4]([Cl:12])[N:3]=1

Participants

3

Reactant 2

HCID 21226129Dichloromethane methanolHCID 866893262,4-Dichloro-5-methoxy-6-vinylpyrimidine

Product 1

HCID 866893302,6-Dichloro-5-methoxypyrimidine-4-carbaldehydeYield 100%

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).

Workup

  1. customOzone gas was bubbled
  2. customThe reaction was quenched with dimethyl sulfide (50 mL)
  3. concentrationconcentrated under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-98d95df3e54a4e2d988943ed8b0da251
Source dataset
uspto-grants-2015_04
Patent number
US09006250B2

Reaction notes

Loading…