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

HRID 332920

Reaction equation

HRID 332920 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%

Conditions

Temperature
-78 °C

Procedure

The solution of 2,6-dichloro-5-methoxy-4-vinyl pyrimidine (50 g, 0.24 mol) in dichloromethane:methanol (4:1, 2 L), prepared by Example 1, was cooled to −78° C. Ozone gas was bubbled through 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 a crude material comprising the title compound (50.5 g, 100% yield); HPLC (85% acetonitrile buffered with 0.1% v/v acetic acid. The title compound was not isolated from the crude material.

Workup

  1. customOzone gas was bubbled through for 5 h
  2. customThe reaction was quenched with dimethyl sulfide (50 mL)
  3. temperatureThe mixture was slowly warmed to room temperature
  4. concentrationconcentrated under reduced pressure at 40° C.
  5. customto provide a crude material

Sources & evidence

ORD record
ord-012f2a2c013c4e5a8396870fe1076f20
Source dataset
uspto-grants-2014_11
Patent number
US08877925B2

Linked notes

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