4-chloro-5H-pyrrolo[3,2-d]pyrimidine → HCID 56849555, compound

HRID 1925972Notes

Reaction equation

HRID 1925972 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.[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[NH2:15]>CN1CCCC1=O.C(=O)([O-])O.[Na+]>[Cl:11][C:12]1[CH:13]=[C:14]([NH:15][C:2]2[C:3]3[NH:10][CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1

Participants

5

Reactant 2

HCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidineHCID 167812123-Chloro-4-(2-pyridylmethoxy)aniline

Product 1

HCID 56849555HCID 56849555, compoundYield 77.6%

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 (63 mg) in 1-methyl-2-pyrrolidone (0.8 mL), was added 3-chloro-4-(pyridin-2-ylmethoxy)aniline (149 mg), and the mixture was heated to 140° C. and stirred for 2 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:ethyl acetate/methanol=10/0→8/2). The object fraction was concentrated under reduced pressure. Chloroform/diisopropyl ether (1/9) was added to the residue, and the resultant precipitate was collected by filtration and dried under reduced pressure to give the title compound (112 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. additionChloroform/diisopropyl ether (1/9) was added to the residue
  8. filtrationthe resultant precipitate was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-ce7c849e7ae742cb929fa2eae7ebd0a3
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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