Methanol → HCID 13424620, compound

HRID 1285192Notes

Reaction equation

HRID 1285192 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[C:10](=[O:15])([O:13][CH3:14])OC.[CH3:16][O-:17].[Na+].[Cl-].[Na+].[CH3:21][OH:22]>O>[Cl:9][C:4]1[N:3]=[C:2]([NH:1][C:16]([O:22][CH3:21])=[O:17])[N:7]=[C:6]([NH:8][C:10]([O:13][CH3:14])=[O:15])[CH:5]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 5234Sodium ChlorideHCID 12021Dimethyl CarbonateHCID 674322,4-Diamino-6-chloropyrimidineHCID 10942334Sodium Methoxide

Product 1

HCID 13424620HCID 13424620, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 144.6 g (1 mol) of 2,4-diamino-6-chloropyrimidine and 2170 ml of dimethyl carbonate is heated to about 80° under nitrogen and while stirring and then treated dropwise over a period of 30 minutes with 373 ml (2 mol) of a 30 percent solution of sodium methylate in methanol, a white suspension resulting. The mixture is thereafter stirred at about 70° for a further hour, poured into a mixture of 3 kg of ice and 1 l of water, treated with 1440 g of sodium chloride and stirred, while cold, for 1 hour. The white precipitation is subsequently separated by suction filtration under a slight vacuum, and the residue is then washed until neutral using three 500 ml portions of ice-cold water. After drying, there is obtained dimethyl 6-chloro-2,4-pyrimidinedicarbamate as a white solid of melting point 156°-158°.

Workup

  1. temperatureis heated to about 80° under nitrogen
  2. customa white suspension resulting
  3. stirringThe mixture is thereafter stirred at about 70° for a further hour
  4. stirringstirred
  5. customThe white precipitation
  6. customis subsequently separated by suction filtration under a slight vacuum
  7. washthe residue is then washed
  8. customAfter drying

Sources & evidence

ORD record
ord-caf8948f65204613b9d8c816798cb1d7
Source dataset
uspto-grants-1986_01
Patent number
US04565869

Reaction notes

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