Dimethylformamide → 4,6-dichloro-N,N-dimethylpyrimidin-2-amine

HRID 2071172Notes

Reaction equation

HRID 2071172 reaction equation
CI.[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=C(N)[N:5]=1.[H-].[Na+].[CH3:14][N:15]([CH:17]=O)[CH3:16]>>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[N:7]=[C:17]([N:15]([CH3:16])[CH3:14])[N:5]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 27636244,6-dichloro-N,N-dimethylpyrimidin-2-amineYield 84%

Conditions

Temperature
0 °C

Procedure

MeI (0.46 ml, 1.04 g, 7.32 mmol, 2.4 eq) was added to a stirred solution of 4,6-dichloropyrimidin-2-amine (Aldrich, 0.5 g, 3.05 mmol, 1 eq) in 10 ml anhydrous DMF under Ar. After cooling to 0° C., NaH (0.27 g, 6.71 mmol, 2.2 eq) was added. The reaction was stirred at 0° C. to room temperature overnight. The reaction was quenched with water and extracted with Et2O (×1). The organic layer was washed with water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.4947 g (2.58 mmol, 84% yield) of 4,6-dichloro-N,N-dimethylpyrimidin-2-amine.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with Et2O (×1)
  3. washThe organic layer was washed with water (×3), brine (×1)
  4. dry with materialdried over Na2SO4
  5. filtrationThe inorganics were filtered off
  6. customthe solvent was removed in vacuo
  7. customPurification via flash chromatography

Sources & evidence

ORD record
ord-b51e77ed6334404ab75e81a37189f82f
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

Loading…