Tetrahydrofuran → N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N,3,3-trimethylbutanamide

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Triethylamine	HCID 8471	—
Reactant	3,3-Dimethylbutanoyl chloride	HCID 81514	—
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	N-(4-{2-[6-(4-chlorophenyl)-4-oxothieno[3,2-d]pyrimidin-3(4H)-yl]ethyl}benzyl)-N,3,3-trimethylbutanamide	HCID 67360222	78.3%

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of the compound (85 mg) obtained in Example 4, 3,3-dimethylbutanoyl chloride (31 mg), triethylamine (53 mg) and tetrahydrofuran (2 ml) was stirred at 60° C. for 3 hr. The reaction mixture was diluted with ethyl acetate, and washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane (2:1, volume ratio) to give the title compound (70 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-553c5b0d3c8b4f8e8677183f9e028a67
Source note	uspto-grants-2011_08