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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 550647Generated: October 30, 2026

Triethylamine → 6-Bromo-2-[(4-methyl-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)carbonyl]pyrazolo[1,5-a]pyrimidine

https://huagongshe.com/reaction/550647

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant6-Bromopyrazolo[1,5-a]pyrimidine-2-carboxylic acidHCID 771938—
ReactantO-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2733207—
Reactant4-Methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridineHCID 6485295—
SolventWaterHCID 962—
SolventAcetonitrileHCID 6342—
Product6-Bromo-2-[(4-methyl-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)carbonyl]pyrazolo[1,5-a]pyrimidineHCID 2489876348%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a solution of 6-bromo-pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (0.7 g, 2.9 mmol, 1.0 equiv) and TBTU (1.0 g, 3.1 mmol, 1.1 equiv) in dry acetonitrile (20 mL), triethylamine (1 mL, 7.25 mmol, 2.5 equiv) and 4-methyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine (0.45 g, 2.9 mmol, 1 equiv) are added. The reaction mixture is stirred at 50° C. for 2 h and then at room temperature for 8 h. The reaction mixture is diluted with water (10 ml). The precipitate is filtered, washed sequentially with 50% aqueous ethanol, water, 5% aqueous ammonia, and diethyl ether, and then dried to provide 0.524 g of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07947689B2
Source datasetuspto-grants-2011_05
ORD IDord-d89a9695ed80473694606d7733426cc9
Source noteuspto-grants-2011_05