Ethanol → HCID 57597231, compound

HRID 1926013Notes

Reaction equation

HRID 1926013 reaction equation
C([C:3]1[N:4]=[C:5](Cl)[C:6]2[NH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)C.[NH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:18]([CH:22]=1)[C:19]([O-:21])=[O:20].CN1CC[CH2:33][C:32]1=O.C(O)C>O>[O:23]([C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:5]2[C:6]3[NH:11][CH:10]=[CH:9][C:7]=3[N:8]=[CH:3][N:4]=2)=[CH:22][C:18]=1[C:19]([O:21][CH2:32][CH3:33])=[O:20])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 13387N-methyl-2-pyrrolidoneHCID 86615757HCID 86615757, compoundHCID 86615758HCID 86615758, compound

Product 1

HCID 57597231HCID 57597231, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (461 mg), 5-amino-2-phenoxybenzoate (926 mg) and 1-methyl-2-pyrrolidone (5 mL) was stirred at 80° C. for 2 hrs. Ethanol, water and activated carbon were added to the reaction mixture and the mixture was stirred. The activated carbon was filtered off, and the solvent was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent, methanol:ethyl acetate=0:100→20:80) and recrystallized from ethanol-ethyl acetate to give the title compound (572 mg) as a colorless powder.

Workup

  1. stirringthe mixture was stirred
  2. filtrationThe activated carbon was filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. additionAqueous sodium hydrogen carbonate solution was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (eluent, methanol:ethyl acetate=0:100→20:80)
  10. customrecrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-6ff2d4d3402949e5b906527d86374eaf
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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