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

HRID 1504929Notes

Reaction equation

HRID 1504929 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.C[OH:14].ClCCl>>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=[O:14])[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-carbaldehyde

Procedure

A solution of 2,6-dichloro-5-methoxy-4-vinyl pyrimidine (6.64 g, 32.5 mmol, prepared by Example 2), in methanol:dichloromethane (1:4, 300 mL), was cooled to −78° C. in a dry ice/acetone bath. Ozone was bubbled into the reaction until the starting material was no longer present according to thin layer chromatography (TLC). Dimethyl sulfide (6 mL) was added. The mixture was concentrated on a rotary evaporator at 0° C. to remove the dichloromethane. This provided an unpurified material comprising the title compound. The title compound was not isolated from the unpurified material.

Workup

  1. customOzone was bubbled into the reaction until the starting material
  2. additionDimethyl sulfide (6 mL) was added
  3. concentrationThe mixture was concentrated on a rotary evaporator at 0° C.
  4. customto remove the dichloromethane
  5. customThis provided an unpurified material

Sources & evidence

ORD record
ord-4749bae9241944f78bd003f7d2678f18
Source dataset
uspto-grants-2015_12
Patent number
US09216958B2

Reaction notes

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