N-Iodosuccinimide → HCID 178433376, compound

Participants

Reaction Steps

With protection from external moisture throughout, 250.3 mg. (2.0 millimoles) of finely powdered 6-methyl-isocytosine is dissolved in 4 ml. of hot glacial acetic acid. While still hot, 450 mg. (2.0 millimoles) of N-iodosuccinimide is added to the solution and the whole is heated on a steam bath for five minutes with occasional swirling. The reaction mixture is removed from the steam bath and allowed to stand at ambient temperature. After three and one-half hours, water is added, the crystalline cake is crushed, the solid collected, washed with water, then acetone and dried in air. The crude material [335 mg.] is crystallized from approximately 10 ml. of glacial acetic acid. After being kept at room temperature overnight, the pure compound is collected, washed with its mother liquor, then with anhydrous ether repeatedly and dried in vacuo at ca. 90°C. There is thus obtained 220 mg. of 2-amino-5-iodo-6-methyl-4-pyrimidinol which melts at 211.5° to 212.5°C. with previous darkening and sintering, has λ max0.1N NaOH 236 nm. (ε9,900); 284 nm. (ε10,900) and the infrared absorption below.

Provenance & Evidence