Ethyl 3-aminobenzoate → HCID 57597372, compound

HRID 1786917Notes

Reaction equation

HRID 1786917 reaction equation
Cl[C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:11][C:12]1[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16].CN1CCCC1=O.C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C>[N:5]1[C:4]2[CH:8]=[CH:9][NH:10][C:3]=2[C:2]([NH:11][C:12]2[CH:13]=[C:14]([CH:20]=[CH:21][CH:22]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:7][CH:6]=1

Participants

7

Reactant 4

HCID 11400Ethyl 3-aminobenzoateHCID 13387N-methyl-2-pyrrolidoneHCID 516892Sodium BicarbonateHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 57597372HCID 57597372, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (2.78 g), ethyl 3-aminobenzoate (4.49 g) and 1-methyl-2-pyrrolidone (20 mL) was stirred at 120° C. for 1.5 hrs. To the reaction mixture were added ethyl acetate, water and saturated aqueous sodium hydrogen carbonate solution. The insoluble material was filtered off, and the ethyl acetate layer was separated. The aqueous layer was extracted with ethyl acetate, and the mixed ethyl acetate layer washed with saturated brine and dried over anhydrous magnesium sulfate. The filtered insoluble material was suspended in methanol and ethyl acetate and saturated brine were added. The ethyl acetate layer was separated. The ethyl acetate layer washed with saturated brine and dried over anhydrous magnesium sulfate. The mixed ethyl acetate layer was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate) and crystallized from methanol-acetone-diisopropyl ether to give the title compound (2.85 g) as a pale-brown powder.

Workup

  1. filtrationThe insoluble material was filtered off
  2. customthe ethyl acetate layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe mixed ethyl acetate layer washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additionethyl acetate and saturated brine were added
  7. customThe ethyl acetate layer was separated
  8. washThe ethyl acetate layer washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationThe mixed ethyl acetate layer was concentrated under reduced pressure
  11. customthe obtained residue was purified by silica gel column chromatography (eluent, ethyl acetate)
  12. customcrystallized from methanol-acetone-diisopropyl ether

Sources & evidence

ORD record
ord-39357e8768c7471a8bd07f459e37468c
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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