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.[OH-].[K+].[CH2:13]([OH:15])[CH3:14]>>[CH2:13]([O:15][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1)[CH3:14]Participants
4
Procedure
To 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 300 mg, 1.95 mmol) in 3.0 mL of ethanol, potassium hydroxide (226 mg, 4.03 mmol) was added and the reaction was microwaved at 120° C. for 3 hours. The reaction was extracted in ethyl acetate and aqueous saturated ammonium chloride. The organic layer was separated and washed with brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was recrystallized with methanol to provide the desired compound (47, 213 mg). MS (ESI) [M+H+]+=164.9.