Methanol → 2-Chloro-5-fluoro-4-methoxypyrimidine
Reaction equation
[Na].[Cl:2][C:3]1[N:8]=[C:7](Cl)[C:6]([F:10])=[CH:5][N:4]=1.[CH3:11][OH:12]>>[Cl:2][C:3]1[N:8]=[C:7]([O:12][CH3:11])[C:6]([F:10])=[CH:5][N:4]=1Participants
4
Procedure
To a mixture of sodium (450 mg, 19 mmol) in methanol (20 mL) was added a solution of 2,4-dichloro-5-fluoropyrimidine (3.25 g, 19 mmol) in methanol (10 mL). The reaction mixture was stirred at room temperature overnight before being partitioned between water and diethyl ether. The organic phase was separated, washed with brine and evaporated to dryness to give the title compound as an orange oil (80%), which was used in the next step without further purification.
Workup
- custombefore being partitioned between water and diethyl ether
- customThe organic phase was separated
- washwashed with brine
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-e2e1c63341dd43758c3406a5c3654b8b
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206183B2
Reaction notes
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