7-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one → 7-({6-[2-(5-Chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-2-oxo-5,6-dihydro-2H-pyran-3-yl}methyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Participants

Reaction Steps

The title compound was prepared as described in Example B(53), using 7-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (prepared according to a reported procedure: Doria, G.; Passarotti, C.; Sala, R.; Magrini, R.; Sberze, P.; Tibolla, M.; Cesarani, R.; Arcari, G.; Castello, R.; Toti, D. Farmaco Ed. Sci. 1985, 40, 885) in place of 5-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazole, and using 6-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione in place of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione. Yield: 18%. 1H NMR (300 MHz, DMSO-d6) δ 1.23-1.73 (m, 8H), 1.78-2.0 (m, 2H), 2.35 (m, 1H), 2.48-2.58 (m, 2H, overlap with DMSO-d5), 2.64 (s, m, overlap, 4H), 2.78 (d, J=18 Hz, 1H), 3.44 (s, 2H), 3.78 (s, 3H, overlap with H2O peak), 3.85 (s, 3H), 5.80 (s, 1H), 6.70 (s, 1H), 6.97 (s, 1H), 7.11 (s, 1H), 10.96 (br s, 1H). LC-MS (APCI) calcd for C28H31ClN2O6S: 558.16; found (M+H+) 559.0 m/z.

Provenance & Evidence