Methanol → 2-Chloro-5-fluoro-4-methoxypyrimidine

HRID 1500750Notes

Reaction equation

HRID 1500750 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]=1

Participants

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

  1. custombefore being partitioned between water and diethyl ether
  2. customThe organic phase was separated
  3. washwashed with brine
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-e2e1c63341dd43758c3406a5c3654b8b
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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