Dimethylformamide → HCID 12021991, compound

HRID 1417157Notes

Reaction equation

HRID 1417157 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2([OH:26])[C:15]3=[N:16][CH:17]=[CH:18][C:19]([C:20]4[O:21][CH:22]=[CH:23][CH:24]=4)=[C:14]3[C:13](=[O:25])[O:12]2)[N:4]=1.[CH3:27]N(C)C=O.C(=O)([O-])[O-].[K+].[K+].CI>O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]([C:15]2[N:16]=[CH:17][CH:18]=[C:19]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)[C:14]=2[C:13]([O:12][CH3:27])=[O:25])=[O:26])[N:4]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 70346543HCID 70346543, compound

Product 1

HCID 12021991HCID 12021991, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.1 g of 7-(4,6-dimethoxypyrimidin-2-yl)-4-(2-furyl)-7-hydroxyfuro[3,4-b]pyridin-5(7H)one was weighed out, and 50 ml of N,N-dimethylformamide and 0.82 g of potassium carbonate were added thereto. The mixture was stirred at room temperature. 0.8 g of methyl iodide was added thereto dropwise, and the mixture was stirred at room temperature overnight, then poured into water and extracted 200 ml of ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/3) to obtain 1.1 g (yield 50.7%) of the desired compound as brown crystals. m.p.: 135°-140° C.

Workup

  1. stirringdropwise, and the mixture was stirred at room temperature overnight
  2. extractionextracted 200 ml of ethyl acetate
  3. washThe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-6842c5c43b094ed198a2e50b8b2cb0f4
Source dataset
uspto-grants-1999_03
Patent number
US05877120

Reaction notes

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