Water → [(R)-1-(6-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethyl]-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-amine

https://huagongshe.com/reaction/1911060

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	4-Chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxide	HCID 59475895	—
Reactant	(1R)-1-(5-chloro-1H-benzimidazol-2-yl)-2-methoxyethylamine	HCID 59708426	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	[(R)-1-(6-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethyl]-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-amine	HCID 59708429	37.8%

Reaction Conditions

Temperature	120 °C

Reaction Steps

200 mg 4-chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxide (cf Example 124), 235 mg (R)-1-(6-chloro-1H-benzimidazol-2-yl)-2-methoxy-ethylamine and 179.62 μl diisopropylethylamine are placed in 4 ml dioxane, and the mixture is heated to 120° C. in the microwave for 0.3 hours. Then the reaction mixture is combined with water and dichloromethane and extracted. The product is purified by semipreparative HPLC (method A). 113 mg of the product are obtained as a powder. Analytical HPLC-MS, (method B): RT=1.88 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08604039B2
Source dataset	uspto-grants-2013_12
ORD ID	ord-4c46f14038a6440397db9f22e429b0ec
Source note	uspto-grants-2013_12