Benzyl Chloride → HCID 67317020, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-(4-fluorobenzyl)-3-hydroxy-9,9-dimethyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrazino[1,2-a]pyrimidine-2-carboxamide (see Example 1) in DMF was added K2CO3 (2 eq.) followed by BnCl (1.1 eq.). The mixture was stirred at 65° C. overnight, after which time additional BnCl (0.3 eq.) was added and the mixture was left for a further 6 hours. The solvent was removed under reduced pressure and the brown oil was taken into EtOAc, washed with 1N HCl and brine, dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography, eluting with 2% MeOH/DCM to afford the title product. 1H NMR (300 MHz, d6-DMSO) δ 8.88 (t, J=6.2 Hz, 1H), 7.30-7.44 (m, 7H), 7.06 (t, J=8.8 Hz, 2H), 5.05 (s, 2H), 4.41 (d, J=6.2 Hz, 2H), 3.80 (t, J=5.4 Hz, 2H), 3.09 (br. s, 2H), 1.44 (s, 6H); MS (ES) C24H25FN4O3 requires 436. Found: 437 (M+H+).

Provenance & Evidence