Ethanol → 4-ethoxy-7H-pyrrolo[2,3-d]pyrimidine
Reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:11]([OH:13])[CH3:12].[OH-].[K+]>>[CH2:11]([O:13][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1)[CH3:12]Participants
4
Conditions
- Temperature
- 120 °C
Procedure
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine (9, 300 mg, 1.95 mmol) is combined with 3.00 mL of ethanol (10, 51.4 mmol), then potassium hydroxide (0.226 g, 4.03 mmol) is added. The reaction is heated at 120° C. for 3 hours in a microwave, then extracted with ethyl acetate and aqueous saturated ammonium chloride. The organic layer is washed with brine, dried with magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is recrystallized from methanol to provide the desired compound (11, 213 mg). MS (ESI) [M+H+]+=164.9.