Hydrochloric Acid → 2-(2-Naphthalen-2-yl-ethoxymethyl)-3H-pteridin-4-one

Participants

Reaction Conditions

Reaction Steps

K2CO3 (442 mg) was added to a solution of 3-chloro-pyrazine-2-carboxylic acid [1-imino-2-(2-naphthalen-2-yl-ethoxy)-ethyl]-amide (590 mg) in DMF (5 ml) and heated to 100° C. for 3 h. The reaction mixture was acidified to pH=5 (aqueous HCl, 1N) and extracted with ethyl acetate. The organic layers were dried (Na2SO4), filtered, and the solvent was evaporated. 2-(2-Naphthalen-2-yl-ethoxymethyl)-3H-pteridin-4-one (170 mg, 32%) was obtained from the residue by column chromatography (silica gel, eluent gradient n-heptane/ethyl acetate=80/20-50/50). MS: m/e=331.0 [M−H−]. 1H NMR (d6-DMSO): δ 3.09 (t, 2H), 3.91 (t, 2H), 4.51 (s, 2H), 7.45-7.50 (m, 3H), 7.79-7.88 (m, 4H), 8.82 (d, 1H), 8.99 (d, 2H), 12.72 (bs, 1H).

Provenance & Evidence