Dimethylamine → Methyl 4-chloro-6-dimethylamino-pyrimidin-5-yl-acetate

HRID 1078192Notes

Reaction equation

HRID 1078192 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[C:10]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:9]([Cl:16])[N:8]=[CH:7][N:6]=1.C(N(CC)CC)C>COCCOC.O>[Cl:16][C:9]1[C:10]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:5]([N:2]([CH3:3])[CH3:1])[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 54165419Methyl 2-(4,6-dichloropyrimidin-5-yl)acetate

Product 1

HCID 53722653Methyl 4-chloro-6-dimethylamino-pyrimidin-5-yl-acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Dimethylamine (50 ml of a 40% aqueous solution) is added dropwise to a solution of methyl 4,6-dichloropyrimidin-5-yl-acetate (80 g, 0.36 mol) in 1,2-dimethoxyethane (300 ml) and triethylamine (56 ml, 0.4 mol) at room temperature with cooling. After stirring for 1 hour the mixture is diluted with water and the product extracted with diethyl ether. Drying (MgSO4), evaporation of the solvent and distillation gives the methyl 4-chloro-6-dimethylamino-pyrimidin-5-yl-acetate as a colorless solid (74 g), b.p. 135°-138° C./1.5 torr, m.p. 30°-32° C.

Workup

  1. temperaturewith cooling
  2. extractionthe product extracted with diethyl ether
  3. customDrying
  4. custom(MgSO4), evaporation of the solvent and distillation

Sources & evidence

ORD record
ord-0c350f21cf8244f5a3dab445f6b3264f
Source dataset
uspto-grants-1996_08
Patent number
US05547919

Reaction notes

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