Dimethylamine → 2-Dimethylaminopyrimidine

HRID 1075454Notes

Reaction equation

HRID 1075454 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 (5g, 43.65mmol) in dry THF (50ml) 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 5.07g (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-e8296edecc6243c580931539ada954ac
Source dataset
uspto-grants-1999_05
Patent number
US05902813

Reaction notes

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