Potassium Hydroxide → 1-Cyclopropylmethylcytosine

Participants

Reaction Steps

To a solution of 4.55 g. of 85% potassium hydroxide in 93 mml. of methanol cooled to 5°, was added 17.0 g. of 5-bromo-1-cyclopropylmethyl-5,6-dihydrocytosine. The mixture was stirred and allowed to warm spontaneously. When the initial reaction, which had warmed the mixture to 30°, subsided, the mixture was refluxed for 5 minutes and allowed to cool and stand at room temperature overnight. The suspension was evaporated under reduced pressure on a water bath at 86°. The residue was triturated was 300 ml. of water on a steam bath and chilled in ice before filtering. The resulting 1-cyclopropylmethylcytosine was washed with cold water and dried in a vacuum desiccator over potassium hydroxide; yield, 9.50 g., m.p. 264°-266°. A sample for analysis was recrystallized from ethanol; m.p. 265°-267°.

Provenance & Evidence