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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 72244Generated: October 27, 2026

Ethyl Acetate → 6-Cyclopropylmethoxymethyl-3-[4-(3-dimethylamino-pyrrolidin-1-yl)-phenyl]-3H-thieno[3,2-d]pyrimidin-4-one

https://huagongshe.com/reaction/72244

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantBromomethylcyclopropaneHCID 81503—
ReactantPotassium tertbutoxideHCID 50987170—
Reactant3-[4-(3-Dimethylamino-pyrrolidin-1-yl)-phenyl]-6-hydroxymethyl-3H-thieno[3,2-d]pyrimidin-4-oneHCID 68975447—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product6-Cyclopropylmethoxymethyl-3-[4-(3-dimethylamino-pyrrolidin-1-yl)-phenyl]-3H-thieno[3,2-d]pyrimidin-4-oneHCID 57625257—

Reaction Conditions

Temperature0 °C

Reaction Steps

A mixture of 3-[4-(3-dimethylamino-pyrrolidin-1-yl)-phenyl]-6-hydroxymethyl-3H-thieno[3,2-d]pyrimidin-4-one (20.0 mg) and potassium-tert.-butoxide (7.65 mg) in DMF (0.3 mL) was stirred at 0° C. for 5 min. Then cyclopropylmethylbromide (11.28 mg) was added. The solution was warmed to room temperature and stirred for 2 h. Then ethyl acetate and water were added. The aqueous phase was extracted several times with ethyl acetate, the combined organic phases dried over sodium sulfate and the solvent removed in vacuo. The crude product was purified by preparative HPLC. The product with the molecular weight of 424.56 (C23H28N4O2S) was obtained in this way; MS (ESI): 425 (M+H+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08828991B2
Source datasetuspto-grants-2014_09
ORD IDord-b2939d550b4b4562a249b2ee576eb368
Source noteuspto-grants-2014_09