Hydrochloric Acid → 4-Chloro-6-methoxy-2-(methylthio)pyrimidine
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[CH3:11][O-:12].[Na+].Cl>CO>[Cl:1][C:2]1[CH:7]=[C:6]([O:12][CH3:11])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4,6-Dichloro-2-(methylthio)pyrimidine (40 g, 205 mmol) was dissolved in methanol (1025 mL) and cooled to 0° C. Sodium methoxide (55.4 g, 1025 mmol) was added slowly and the mixture was stirred at room temperature for 18 h. 300 mL of 3 M HCl was added and the methanol was evaporated. Additional water (500 mL) was added and the mixture was filtered, washed with water and dried to give the title compound as a white solid. 1H NMR (CDCl3) δ 6.41 (s, 1H), 3.97 (s, 3H), 2.55 (s, 3H); LCMS 2.40 min, 191 (M+H).
Workup
- customthe methanol was evaporated
- additionAdditional water (500 mL) was added
- filtrationthe mixture was filtered
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-8bf095d96918451b8e2dce2fd00c7320
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221809B2
Reaction notes
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