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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 324415Generated: October 25, 2026

Boron trifluoride etherate → (+/-)-5-(7-Ethyl-9,10-dihydro-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-2,4(1H,3H)-pyrimidinedione

https://huagongshe.com/reaction/324415

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBoron trifluoride etherateHCID 8000—
ReactantTriethylsilaneHCID 12052—
ReactantSodium BicarbonateHCID 516892—
Reactant(+/-)-4-(2,4-Bis(1,1-dimethylethoxy)pyrimidin-5-yl)-7-ethyl-2-methyl-9,10-dihydro-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-olHCID 70113732—
SolventDichloromethaneHCID 6344—
Product(+/-)-5-(7-Ethyl-9,10-dihydro-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-yl)-2,4(1H,3H)-pyrimidinedioneHCID 70114236—

Reaction Conditions

Temperature0 °C

Reaction Steps

A stirred solution of the product from step (i) (0.60 g) in dichloromethane (15 ml) was treated with triethylsilane (0.225 ml) and cooled to 0° C. Boron trifluoride etherate (0.65 ml) was added in four equal portions at 5 minute intervals and the reaction stirred at room temperature for 16 hours. The reaction was poured into saturated sodium bicarbonate solution (200 ml) and extracted with ethyl acetate. The extracts were dried (MgSO4) and evaporated to give a yellow solid which was purified by reverse phase chromatography eluting with 50% to 80% methanol in 0.1% aqueous ammonium acetate.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06218376B1
Source datasetuspto-grants-2001_04
ORD IDord-81e57e3676454468b17fdd38b48e4ab2
Source noteuspto-grants-2001_04