Methyl iodide → HCID 14547451, compound

HRID 1589147Notes

Reaction equation

HRID 1589147 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[C:4]([CH2:9][O:10][CH2:11][C:12]2[NH:13][C:14]([CH3:35])=[C:15]([C:31]([O:33][CH3:34])=[O:32])[CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=3[Cl:30])[C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:3]=1.IC.[C:38](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[NH2:1][C:2]1[N:7]([CH3:38])[C:6](=[O:8])[CH:5]=[C:4]([CH2:9][O:10][CH2:11][C:12]2[NH:13][C:14]([CH3:35])=[C:15]([C:31]([O:33][CH3:34])=[O:32])[CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=3[Cl:30])[C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136185985HCID 136185985, compound

Product 1

HCID 14547451HCID 14547451, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-6-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}-4-pyrimidone (0.52 g), iodomethane (0.14 g) and potassium carbonate (0.14 g) in dimethylformamide (20 ml) was stirred at room temperature for 4 days and then evaporated. The residue was partitioned between chloroform and water and the organic layer washed twice with water, dried over anhydrous magnesium sulphate and evaporated. The residue was crystallised from ethyl acetate to give the title compound (0.23 g), m.p. 202°-205° C. Found: C,53.42; H,4.87; N,10.49. C24H26Cl2N4O6 requires C,53.64; H,4.88; N,10.43%.

Workup

  1. customevaporated
  2. customThe residue was partitioned between chloroform and water
  3. washthe organic layer washed twice with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated
  6. customThe residue was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-b8231dc83855435fabd695b1e6642767
Source dataset
uspto-grants-1986_02
Patent number
US04568677

Reaction notes

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