7-(chloromethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one → 7-[(6-{2-[3-Chloro-4-(cyclopropylmethoxy)phenyl]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-(3-Chloro-4-cyclopropylmethoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione	HCID 58762670	—
Product	7-[(6-{2-[3-Chloro-4-(cyclopropylmethoxy)phenyl]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 58762603	1%

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-{-[3-chloro-4-(cyclopropylmethoxy)phenyl]ethyl}-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione (from Step 4, below) in place of 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione. Yield: 1%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07148226B2
Source dataset	uspto-grants-2006_12
ORD ID	ord-98e891c3221c4dceafbbbff601554588
Source note	uspto-grants-2006_12