Ammonia → HCID 59299542, compound

Participants

Reaction Steps

A stirred solution of 1,3-dibutyl-2,6-dioxo-7-(2-propen-1-yl)-2,3,6,7-tetrahydro-1H-purine-8-carboxylic acid (1.0 g, 2.9 mmol) in anhydrous DMF (10 ml) was sequentially treated with DIPEA (1.1 ml), PyBOP, and 2M NH3 (3.6 ml). After 2 hours the product mixture was partitioned between 2M HCl(aq) and EtOAc. The organic layer was separated, washed with sat. NaHCO3(aq) solution, brine, then dried (MgSO4) and concentrated giving an orange oil (ca. 2 g). The product was purified by Biotage™ chromatography eluting with 5%→40% EtOAc/cyclohexane mixtures. The appropriate fractions were combined and concentrated to give the amide 90% pure (790 mg, 78%). m/z. 392.3[M+formic acid−H]−.

Provenance & Evidence