Allyl iodide → 4-Chloro-7-(prop-2-en-1-yl)-7H-pyrrolo[2,3-d]pyrimidine

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Reaction Steps

To 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.3 g: 8.5 mmol) in dry THF (30 ml) was added sodium hydride (1.0 g, 0.25 mmol, 60% dispersion in mineral oil). After stirring at ambient temperature for 1 hour, allyl iodide (0.93 ml, 10 mmol) was added and stirring continued for 48 hours. The mixture was concentrated in vacuo, triturated in hot ethyl acetate, and filtered. The filtrate was concentrated in vacuo to give an orange solid residue. The solid was triturated in CH2Cl2 and filtered to afford 4-chloro-7-allyl-pyrrolo[2,3-d]pyrimidine as a light yellow powder (0.58 g, 36%): TS-MS: 194 (MH+).

Provenance & Evidence