Imidazole → HCID 13424620, compound

HRID 1285196Notes

Reaction equation

HRID 1285196 reaction equation
N1C=CN=C1.[H-].[Na+].[H][H].Cl[C:11]([O:13][CH3:14])=[O:12].[Cl:15][C:16]1[N:21]=[C:20]([NH2:22])[N:19]=[C:18]([NH2:23])[CH:17]=1>O1CCCC1.CN(C)C=O.CO>[Cl:15][C:16]1[N:21]=[C:20]([NH:22][C:11]([O:13][CH3:14])=[O:12])[N:19]=[C:18]([NH:23][C:11]([O:13][CH3:14])=[O:12])[CH:17]=1

Participants

9

Reactant 5

HCID 795ImidazoleHCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 674322,4-Diamino-6-chloropyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 13424620HCID 13424620, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2.7 g (0.041 mol) of imidazole in 50 ml of dry tetrahydrofuran is treated at 0° C. with 1.8 g (0.041 mol) of 55 to 60 percent sodium hydride. After the hydrogen formation has finished, 3.8 g (0.041 mol) of methyl chloroformate in 20 ml of dry tetrahydrofuran are added dropwise at 0° C., whereupon the suspension obtained is treated dropwise at 0° with a solution of 2.9 g (0.021 mol) of 6-chloro-2,4-diaminopyrimidine and 4.5 g (0.041 mol) of potassium t-butylate in 30 ml of dry dimethylformamide. The mixture is stirred at 0° for 1 hour and then at 50° for 3 hours, whereupon 3 ml of methanol are added thereto and the solvent is evaporated to the largest extent possible. The residue is poured into ice-cold water, adjusted with 1N hydrochloric acid to pH 2 and extracted with methylene chloride and a small amount of methanol. After drying the organic extract over magnesium sulphate and evaporation under vacuum, the residue is recrystallized from ethyl acetate, there being obtained pure dimethyl 6-chloro-2,4-pyrimidinedicarbamate.

Workup

  1. customobtained
  2. waitat 50° for 3 hours
  3. customthe solvent is evaporated to the largest extent possible
  4. additionThe residue is poured into ice-cold water
  5. extractionextracted with methylene chloride
  6. customAfter drying the
  7. extractionorganic extract over magnesium sulphate and evaporation under vacuum
  8. customthe residue is recrystallized from ethyl acetate, there

Sources & evidence

ORD record
ord-ca4b0dc123fb429f9e12919bbab8e6de
Source dataset
uspto-grants-1986_01
Patent number
US04565869

Reaction notes

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