Water → 4-Chloro-6-(furan-2-yl)-5-methyl-5H-pyrrolo[3,2-d]pyrimidine

HRID 1786942Notes

Reaction equation

HRID 1786942 reaction equation
[Cl:1][C:2]1[C:3]2[NH:10][C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:16](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[Cl:1][C:2]1[C:3]2[N:10]([CH3:16])[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 713033474-chloro-6-(furan-2-yl)-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 714134594-Chloro-6-(furan-2-yl)-5-methyl-5H-pyrrolo[3,2-d]pyrimidineYield 40.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-6-(2-furyl)-5H-pyrrolo[3,2-d]pyrimidine (220 mg) in N,N-dimethylformamide (2.5 mL) were added potassium carbonate (139 mg) and methyl iodide (0.25 mL) and the mixture was stirred at room temperature for 8 hrs. The mixture was poured into water (30 mL) and extracted with ethyl acetate (30 mL×3). The organic layers were combined and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=4:1→0:1) to give the title compound (94 mg).

Workup

  1. extractionextracted with ethyl acetate (30 mL×3)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationAfter concentration under reduced pressure

Sources & evidence

ORD record
ord-4b3bfb9f6ba64d338b3412fe35f0ed62
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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