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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1396730Generated: October 27, 2026

1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Amino-2-[2-(4-fluorophenyl)ethyl]-7-(4-(2-phenoxyethyl)piperazin-1-yl)-thiazolo[5,4-d]pyrimidine

https://huagongshe.com/reaction/1396730

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
ReactantBenzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 151348—
Reactant1-(2-Phenoxyethyl)piperazineHCID 233187—
Reactant5-amino-2-[2-(4-fluorophenyl)ethyl]-6H-thiazolo[5,4-d]pyrimidin-7-oneHCID 66758061—
SolventDimethylformamideHCID 6228—
Product5-Amino-2-[2-(4-fluorophenyl)ethyl]-7-(4-(2-phenoxyethyl)piperazin-1-yl)-thiazolo[5,4-d]pyrimidineHCID 4691685125.4%

Reaction Steps

To a solution of 5-amino-2-[2-(4-fluorophenyl)ethyl]-6H-thiazolo[5,4-d]pyrimidin-7-one (133 mg, 0.46 mmol) in DMF (5 ml) was added DBU (0.69 mmol), BOP (0.59 mmol) and 1-(2-phenoxyethyl)piperazine (1.37 mmol). The reaction mixture was stirred at room temperature for 3 hours whereupon the solvent was removed in vacuo. The resulting residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 100% CH2Cl2 to 2% CH3OH in CH2Cl2), yielding the pure title compound (56 mg) which was characterized by its mass spectrum: MS m/z (%): 479 ([M+H]+, 100).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08901132B2
Source datasetuspto-grants-2014_12
ORD IDord-b15296af4cc64e6c9726342db20baf72
Source noteuspto-grants-2014_12