Sodium Thiosulfate → HCID 86607542, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 2-[5-(hydroxymethyl)pyrimidin-2-yl]-1,2,3,4-tetrahydro-9H-b-carboline-9-carboxylate (2.0 g, 0.0053 moles) in dry DCM (20 mL) was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (2.68 g, 0.0063 moles). After stirring for 5.0 hours, Na2S2O3 (1.0 g), NaHCO3 (1.0 g) in water (15 mL) was added. The two layers were separated. The organic layer was washed with water (20 mL), dried (Na2SO4) and concentrated. The crude product was crystallized using mixture of diethyl ether-hexane to give pure tert-butyl 2-[5-(formyl)pyrimidin-2-yl]-1,2,3,4-tetrahydro-9H-b-carboline-9-carboxylate (1.4 g, 74% yield). Rf=0.4. 1H NMR (DMSO-d6, 400 MHz) ppm: 9.8 (s, 1H, CHO), 8.8 (s, 2H, 2Ar—H), 8.06 (d, 1H, J=8 Hz, 1Ar—H), 7.52 (d, 1H, J=8 Hz, 1Ar—H), 7.33-7.24 (m, 2H, 2Ar—H), 5.32 (s, 2H, CH2), 4.28 (t, 2H, J=8 Hz, CH2), 2.82 (t, 2H, J=8 Hz, CH2), 1.69 (s, 3H, 3CH3); m/e=379 (M+1) (M, 378.425 Calcd. for C21H22N4O3).

Provenance & Evidence