Methyl iodide → HCID 69849171, compound

HRID 393152Notes

Reaction equation

HRID 393152 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH:9]([NH2:13])[CH:10]([CH3:12])[CH3:11])=[C:7]([O:14][CH3:15])[N:6]=[CH:5][N:4]=1.CI.[CH2:18](N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+].[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39](Cl)=[O:40])=[CH:34][CH:33]=1>O.C(#N)C.CN(C)C(=O)C>[Cl:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][C:39]([N:13]([CH:9]([C:8]2[C:7]([O:14][CH3:15])=[N:6][CH:5]=[N:4][C:3]=2[O:2][CH3:1])[CH:10]([CH3:11])[CH3:12])[CH3:18])=[O:40])=[CH:34][CH:33]=1

Participants

9

Reactant 5

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 906924-Chlorophenylacetyl chlorideHCID 69851675HCID 69851675, compound

Product 1

HCID 69849171HCID 69849171, compoundYield 34.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

0.80 g (3.8 mmol) of 1-(4,6-dimethoxypyrimidin-5-yl)-2-methylpropylamine, 0.59 g (4.2 mmol) of methyl iodide and 0.46 g (4.6 mmol) of triethylamine were added to 10 ml of N,N-dimethylacetamide and reacted at 80° C. for 1 hour. After completion of the reaction, the product was poured into water and extracted with toluene. The organic layer was washed with water and an aqueous sodium chloride solution in this order, dried and concentrated, and the obtained oily product was supplied to the subsequent reaction without purification. 0.20 g (0.89 mmol) of this oily product and 0.22 g (1.6 mmol) of potassium carbonate were added to 20 ml of acetonitrile, and then 0.30 g (1.6 mmol) of 4-chlorophenylacetyl chloride was added at room temperature and reacted overnight. After completion of the reaction, the product was poured into water and extracted with ethyl acetate. The organic layer was washed with an aqueous citric acid solution, water and an aqueous sodium chloride solution in this order, dried and concentrated, and the obtained oily product was purified by preparative HPLC (ethyl acetate:n-hexane=1:1) to obtain 0.21 g (yield: 15%, 2 steps) of 2-(4-chlorophenyl)-N-[1(4,6-dimethoxypyrimidin-5-yl)-2-methylpropyl]-N-methyl acetamide as colorless crystals (melting point: 107-109° C.).

Workup

  1. customreacted at 80° C. for 1 hour
  2. customAfter completion of the reaction
  3. extractionextracted with toluene
  4. washThe organic layer was washed with water
  5. dry with materialan aqueous sodium chloride solution in this order, dried
  6. concentrationconcentrated
  7. customthe obtained oily product was supplied to the subsequent reaction without purification
  8. customreacted overnight
  9. customAfter completion of the reaction
  10. extractionextracted with ethyl acetate
  11. washThe organic layer was washed with an aqueous citric acid solution, water
  12. dry with materialan aqueous sodium chloride solution in this order, dried
  13. concentrationconcentrated
  14. customthe obtained oily product was purified by preparative HPLC (ethyl acetate:n-hexane=1:1)

Sources & evidence

ORD record
ord-5e822ea25e6341a8bc49e298add3e7d7
Source dataset
uspto-grants-2004_10
Patent number
US06806230B1

Reaction notes

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