Methyl iodide → HCID 67974645, compound

Participants

Reaction Conditions

Reaction Steps

A 60% dispersion of sodium hydride in mineral oils (8.6 mg, 0.21 mmol) was added to a solution of (rac)-5-(2-hydroxy-propyl)-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (54 mg, 0.18 mmol) in THF (1 mL) at 0° C. The mixture was stirred at 0° C. for 15 minutes and then iodomethane (0.02 mL, 0.36 mmol) was added and the mixture was allowed to warm to room temperature and stirred for 16 hours. The reaction was quenched with a saturated solution of NH4Cl and extracted with AcOEt, dried with (Na2SO4), filtered and the solvent evaporated in vacuo to yield a yellow oil which was purified by flash column chromatography (silica; AcOEt in heptane from 0:100 to 0:100) to yield a colourless oil which was triturated with DIPE to yield (rac)-5-(2-methoxy-propyl)-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (28 mg, 49% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 1.17 (d, J=6.4 Hz, 3H), 3.27 (dd, J=14.0, 7.9 Hz, 1H), 3.33 (s, 3H), 3.60-3.69 (m, 1H), 3.79-3.85 (m, 1H), 3.85-3.90 (m, 1H), 3.93-4.02 (m, 1H), 4.36 (t, J=6.2 Hz, 2H), 5.09 (s, 2H), 6.93 (s, 1H), 6.96 (t, J=7.4 Hz, 1H), 7.00 (d, J=8.1 Hz, 2H), 7.27-7.32 (m, 2H).

Provenance & Evidence