Sodium → 2-Amino-4-(2,2-dichlorovinyl)-6-methoxypyrimidine

HRID 3909Notes

Reaction equation

HRID 3909 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH:9]=[C:10]([Cl:12])[Cl:11])[N:3]=1.[CH3:13][O-:14].[Na+].[Na]>CO>[NH2:1][C:2]1[N:3]=[C:4]([CH:9]=[C:10]([Cl:12])[Cl:11])[CH:5]=[C:6]([O:14][CH3:13])[N:7]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 201535042-Amino-4-chloro-6-(2,2-dichlorovinyl)pyrimidine

Product 1

HCID 201535032-Amino-4-(2,2-dichlorovinyl)-6-methoxypyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

22.0 Parts of 2-amino-4-chloro-6-(2,2-dichlorovinyl)pyrimidine was dissolved in 500 parts of dry methanol and stirred whilst a solution of sodium methoxide, prepared by dissolving 4.6 parts of sodium in 200 parts of dry methanol, was added dropwise, over 30 minutes at ambient temperature. The resulting solution was stirred for 4 hours by which time all the starting material had been consumed. The product was precipitated by the addition of water, filtered and dried. The solid obtained was purified by chromatography on silica using diethyl ether as eluent. Final purification was effected by recrystallisation from carbon tetrachloride to give 2-amino-4-(2,2-dichlorovinyl)-6-methoxypyrimidine m.p. 90°-91° C.

Workup

  1. customprepared
  2. additionwas added dropwise, over 30 minutes at ambient temperature
  3. customhad been consumed
  4. customThe product was precipitated by the addition of water
  5. filtrationfiltered
  6. customdried
  7. customThe solid obtained
  8. customwas purified by chromatography on silica
  9. customFinal purification
  10. customwas effected by recrystallisation from carbon tetrachloride

Sources & evidence

ORD record
ord-c486bd8087ef4bc39cbd7955c7ea7c4c
Source dataset
uspto-grants-1988_02
Patent number
US04723006

Reaction notes

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