2-Amino-4,6-dichloropyrimidine → 2-Pyrimidinamine, 4-chloro-6-methoxy-

HRID 236522

Reaction equation

HRID 236522 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[O:10]([CH3:12])[Na]>CO>[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([O:10][CH3:12])[N:3]=1

Participants

4

Reactant 2

HCID 655222-Amino-4,6-dichloropyrimidineHCID 178418582HCID 178418582, compound

Product 1

HCID 798112-Pyrimidinamine, 4-chloro-6-methoxy-Yield 58.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

16.4 g 2-amino-4,6-dichloropyrimidine (purchased from Aldrich Chemical Co., Milwaukee, WI 53201) was added to 200 ml of CH3OH. The mixture was cooled to 10° with an ice bath and 5.4 g of NaOCH3 was added in portions while maintaining the temperature. The reaction mixture was allowed to warm to ambient temperature and then heated to reflux for two hours. The reaction mixture was then allowed to cool to ambient temperature and it was stirred overnight. A yellow solid was filtered and recrystallized from butyl chloride. The resulting solid was chromatographed on a dry column of silica, and eluted with 40% EtOAc-hexane. The resulting yellow solid was further purified by recrystallization from butyl chloride. 9.4 g of product with m.p. 163°-166° was obtained.

Workup

  1. temperatureThe mixture was cooled to 10° with an ice bath
  2. temperaturewhile maintaining the temperature
  3. temperatureheated
  4. temperatureto reflux for two hours
  5. temperatureto cool to ambient temperature
  6. filtrationA yellow solid was filtered
  7. customrecrystallized from butyl chloride
  8. customThe resulting solid was chromatographed on a dry column of silica
  9. washeluted with 40% EtOAc-hexane
  10. customThe resulting yellow solid was further purified by recrystallization from butyl chloride

Sources & evidence

ORD record
ord-ee5ef647ba9145258b7fcb273b2f1c5e
Source dataset
uspto-grants-1987_02
Patent number
US04645530

Linked notes

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