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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1844366Generated: October 29, 2026

Sodium hydride → (R)-tetrahydrofuran-3-yl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

https://huagongshe.com/reaction/1844366

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant(-)-3-HydroxytetrahydrofuranHCID 641512—
Reactant4-Nitrophenyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylateHCID 86697451—
SolventTetrahydrofuranHCID 8028—
SolventEthyl AcetateHCID 8857—
Product(R)-tetrahydrofuran-3-yl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylateHCID 8669745272%

Reaction Steps

To 112 mg (0.25 mmol) of 4-nitrophenyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate dissolved in 10 mL of THF, was added (R)-tetrahydrofuran-3-ol (44 mg, 0.5 mmol), followed by 60% NaH (40 mg, 1.0 mmol) and stirred at RT for 2 hr. After 2 hr it was diluted with 20 mL of EtOAc and slowly quench with brine. The organic layer was dried over MgSO4 and concentrated, it was purified over 12 gram silica gel column eluting with 0-10% MeOH/DCM to obtain 71 mg (72% yield) of the desired product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08946415B2
Source datasetuspto-grants-2015_02
ORD IDord-43b4d1aed27d49afa3cc8f62a2804360
Source noteuspto-grants-2015_02