Dimethylamine → 2-Dimethylaminopyrimidine

HRID 581930Notes

Reaction equation

HRID 581930 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][NH:9][CH3:10]>C1COCC1>[CH3:8][N:9]([CH3:10])[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 744042-Chloropyrimidine

Product 1

HCID 5217172-Dimethylaminopyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloropyrimidine (5 g, 43.65 mmol) in dry THF (50 ml) is saturated with gaseous dimethylamine. The mixture is stirred at ambient temperature for 1 hour followed by evaporation of solvent. The residue is partitioned between water and ethyl acetate. The aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and evaporated to leave the product as a brownish oil. Yield 5.07 g (94%).

Workup

  1. customfollowed by evaporation of solvent
  2. customThe residue is partitioned between water and ethyl acetate
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-9f0626bf6d374c4db0d12f2bb86d08c1
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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