Dimethylformamide → 4-chloro-6-methoxy-N,N-dimethylpyrimidin-2-amine

HRID 2071016Notes

Reaction equation

HRID 2071016 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=C(N)[N:5]=1.CI.[CH3:15][N:16]([CH:18]=O)[CH3:17]>>[Cl:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[C:18]([N:16]([CH3:15])[CH3:17])[N:5]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 798112-Pyrimidinamine, 4-chloro-6-methoxy-

Product 1

HCID 7375984-chloro-6-methoxy-N,N-dimethylpyrimidin-2-amineYield 38%

Procedure

NaH (60% dispersion in oil, 0.201 g, 5.02 mmol, 2 eq) was added to a stirred solution of 4-chloro-6-methoxypyrimidin-2-amine (0.400 g, 2.51 mmol, 1 eq, Aldrich) and MeI (0.5 ml, 1.07 g, 7.52 mmol, 3 eq) in 2 ml anhydrous DMF at 0° C. After 1 h the reaction was quenched with water and diluted with EtOAc. The layers were separated. 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 0.180 g (0.96 mmol, 38% yield) of 4-chloro-6-methoxy-N,N-dimethylpyrimidin-2-amine.

Workup

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

Sources & evidence

ORD record
ord-416eeb6b5fcc493698e7ef3d37238af0
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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