1-Phenethylamine, (+)- → 2-[((R)-1-phenyl-ethylamino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one

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Reaction Conditions

Reaction Steps

To 2-chloromethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (50 mg, 0.249 mmol) in ethanol (2 mL) was added (R)-1-phenyl-ethylamine (66 mg, 0.545 mmol, 2 eq) and the solution was heated at 65° C. for 15 h. The cooled solution was concentrated under vacuum and the resulting oil was taken up in methanol, added to a strong cation exchange (SCX) column and washed with methanol (50 mL). The product was eluted with 1 N ammonia in methanol (50 mL) and concentrated under vacuum. The crude product was absorbed onto Silica Gel (500 mg), added to a Biotage SNAP-10 g column and eluted with 1% to 10% methanol in dichlormethane over 12 column volumes to give: 2-[((R)-1-phenyl-ethylamino)-methyl]-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one (20 mg, 28% yield). Exact mass calculated for C16H19N3O2 285.15. found 286.5 (ESI, M+H).

Provenance & Evidence