Water → 4-Chloro-5-(2-ethoxyethyl)-6-(2-furanyl)-5H-pyrrolo[3,2-d]pyrimidine

HRID 1926031Notes

Reaction equation

HRID 1926031 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(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22]([O:24][CH2:25][CH2:26]Br)[CH3:23].O>CN(C)C=O>[Cl:1][C:2]1[C:3]2[N:10]([CH2:23][CH2:22][O:24][CH2:25][CH3:26])[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 10796Cesium carbonate2×HCID 611412-Bromoethyl ethyl ether2×HCID 713033474-chloro-6-(furan-2-yl)-5H-pyrrolo[3,2-d]pyrimidine

Product 1

HCID 860847954-Chloro-5-(2-ethoxyethyl)-6-(2-furanyl)-5H-pyrrolo[3,2-d]pyrimidine

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 (1.2 mL) was added cesium carbonate (489 mg) under ice-cooling, and the mixture was stirred under ice-cooling for 15 min. 2-Bromoethyl ethyl ether (0.169 mL) was added and the mixture was stirred at room temperature for 2 days. Cesium carbonate (326 mg) and 2-bromoethyl ethyl ether (0.113 mL) were added and the mixture was stirred at room temperature for 1 day. The reaction mixture was poured into water (30 mL) and extracted with ethyl acetate (60 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent, hexane:ethyl acetate=4:1→1:4) to give the title compound (76 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 15 min
  3. stirringthe mixture was stirred at room temperature for 2 days
  4. stirringthe mixture was stirred at room temperature for 1 day
  5. extractionextracted with ethyl acetate (60 mL)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-596f1c59809542ba8078a6328517152c
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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