4-chloro-5H-pyrrolo[3,2-d]pyrimidine → HCID 57597349, compound

HRID 1925975Notes

Reaction equation

HRID 1925975 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]=[CH:14][C:15]([O:23][C:24]2[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])[CH:25]=2)=[C:16]([CH:22]=1)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN1CCCC1=O.C(=O)([O-])O.[Na+]>[Cl:30][C:28]1[CH:29]=[C:24]([CH:25]=[C:26]([Cl:31])[CH:27]=1)[O:23][C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:2]2[C:3]3[NH:10][CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:22][C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 2

HCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidineHCID 63423601HCID 63423601, compound

Product 1

HCID 57597349HCID 57597349, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (61 mg) in 1-methyl-2-pyrrolidone (0.8 mL), was added ethyl 5-amino-2-(3,5-dichlorophenoxy)benzoate (186 mg), and the mixture was heated to 140° C. and stirred for 2.5 hrs. The reaction mixture was allowed to cool to room temperature, diluted with 5% aqueous sodium hydrogen carbonate solution (20 mL), and extracted with a mixed solvent (25 mL×3) of ethyl acetate/tetrahydrofuran (1/1). The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (basic silica gel, eluent:hexane/ethyl acetate=8/2→0/10). The object fraction was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the resultant precipitate was collected by filtration and dried under reduced pressure to give the title compound (149 mg) as pale-yellow powder crystals.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with a mixed solvent (25 mL×3) of ethyl acetate/tetrahydrofuran (1/1)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe object fraction was concentrated under reduced pressure
  7. additionEthyl acetate was added to the residue
  8. filtrationthe resultant precipitate was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-c2f74d70edec46caa9c4d6776658b0bd
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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