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

Role	Name	HCID	Charge
Reactant	7-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one	HCID 4354134	—
Reactant	5-(chloromethyl)-1,3-dimethyl-1H-1,2,4-triazole	HCID 13103100	—
Reactant	6-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dione	HCID 16728701	—
Product	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	HCID 58762384	18%

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%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07148226B2
Source dataset	uspto-grants-2006_12
ORD ID	ord-b660e9a32cfd41588b25361688c3df25
Source note	uspto-grants-2006_12