Ethyl chloroformate → HCID 13424621, compound

HRID 1285198Notes

Reaction equation

HRID 1285198 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.Cl[C:11]([O:13][CH2:14][CH3:15])=[O:12]>CN(C)C=O.C(N(CC)CC)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:5]=[C:4]([NH:9][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:3]=1

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 674322,4-Diamino-6-chloropyrimidine

Product 1

HCID 13424621HCID 13424621, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 7.25 g (50 mmol) of 6-chloro-2,4-diaminopyrimidine in 100 ml of dimethylformamide and 20 ml of triethylamine is cooled to 0° and treated dropwise with 10 ml of ethyl chloroformate. The mixture is stirred at room temperature for 70 hours, the precipitated material is filtered off under suction, the filtrate is evaporated and the residue is taken up in methylene chloride. The organic phase is washed with 1N hydrochloric acid, dried over magnesium sulphate and evaporated under vacuum. The crude product obtained is chromatographed on silica gel, there being obtained pure diethyl 6-chloro-2,4-pyrimidinedicarbamate of melting point 153°-154°.

Workup

  1. filtrationthe precipitated material is filtered off under suction
  2. customthe filtrate is evaporated
  3. washThe organic phase is washed with 1N hydrochloric acid
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under vacuum
  6. customThe crude product obtained
  7. customis chromatographed on silica gel, there

Sources & evidence

ORD record
ord-f5fbb103619342979f5895343e2135cc
Source dataset
uspto-grants-1986_01
Patent number
US04565869

Reaction notes

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