Chloroacetyl chloride → 2-chloro-N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylacetamide

Participants

Role	Name	HCID	Charge
Reactant	Chloroacetyl chloride	HCID 6577	—
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Triethylamine	HCID 8471	—
Reactant	6-(4-chlorophenyl)-3-(2-{4-[(methylamino)methyl]phenyl}ethyl)thieno[3,2-d]pyrimidin-4(3H)-one dihydrochloride	HCID 67359698	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2-chloro-N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N-methylacetamide	HCID 59239830	64.5%

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of the compound (200 mg) obtained in Example 4, chloroacetyl chloride (51 mg), triethylamine (146 mg) and tetrahydrofuran (2 ml) was stirred at 60° C. for 1 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography [developing solvent:ethyl acetate-methanol (20:1, volume ratio)] and crystallized from hexane to give the title compound (130 mg) as a colorless powder.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07989445B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-5ad54534f75d4252ba8ceea86b15a4f9
Source note	uspto-grants-2011_08