Ethyl Acetate → HCID 86651562, compound

Participants

Reaction Steps

2-Chloro-6a-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (0.846 g, 3.32 mmol) and (bromomethyl)cyclopropane (0.672 g, 4.98 mmol) were mixed in DMSO (5 ml). Potassium carbonate (0.918 g, 6.64 mmol) was added. The mixture was stirred for 30 minutes at room temperature and then for 2 hours at 35° C. EtOAc (40 ml) was added followed by addition of water (30 ml). Aqueous phase was separated and extracted with EtOAc (2×30 ml). The combined organic phase was washed with water (2×20 ml). The organic solution was concentrated to near dryness at which point a solid had precipitated out. EtOAc (5 ml) and hexanes (20 ml) were added and the mixture was stirred for 20 minutes. The solid was collected by filtration to afford 1.35 g product as a white solid. Concentration and crystallization of mother liquor afforded another 0.28 g of compound as second crop. 1H NMR (400 MHz, CDCl3) δ=0.34 (m, 2H), 0.46 (m, 2H), 1.13 (m, 1H), 1.39 (s, 3H), 3.21 (m, 1H), 3.55 (m, 1H), 3.66 (d, 1H), 3.77 (m, 1H), 3.85-4.02 (m, 4H), 8.20 (s, 1H)

Provenance & Evidence