Guanidine Hydrochloride → 4-(1,1-Dimethoxyethyl)pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

To guanidine hydrochloride salt (15 g, 156.68 mmol) was added sodium ethoxide, 21% wt in EtOH (59 mL, 156.68 mmol). After stirring for 5 min, 1-dimethylamino-4,4-dimethoxy-pent-1-en-3-one (Lipinski; J. Het. Chem., 22:1723 (1995)) (29.30 g, 156.68 mmol) in EtOH (50 mL) was added. The mixture was heated at 80° C. under N2 for 20 h, then cooled to RT. Solvent was evaporated in vacuo and the residue was re-dissolved in hot EtOAc (200 mL). The undissolved solid was separated by filtration and the solvent was evaporated in vacuo to give a pale yellow solid. MS m/z:184.3(M+H). Calc'd for C8H14N3O2: 184.21.

Provenance & Evidence