(R)-ethyl 4-chloro-2-(tetrahydro-2H-pyran-4-ylamino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine-7-carboxylate → (R)-ethyl 2-(tetrahydro-2H-pyran-4-ylamino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine-7-carboxylate

Participants

Reaction Steps

A solution of 404 (0.525 g, 1.23 mmol) and EtOAc (15 mL) was subjected to vacuum/nitrogen purge cycles then Pd/C (0.392 g, 0.369 mmol, 10% Degussa) was added and the solution stirred for 2 h under H2 (H2 balloon). The mixture was filtered and the solid washed with EtOAc and the filterate passed through a 0.45 micron frit and then concentrated. The crude product was purified by SiO2 chromatography eluting with MeOH/DCM (5:95) to afford 0.32 g (77%) of (R)-ethyl 2-(tetrahydro-2H-pyran-4-ylamino)-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine-7-carboxylate (406) as a clear oil: MS m/z (APCI-pos) M+1=308.1.

Provenance & Evidence