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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 718321Generated: October 30, 2026

1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-Ethoxy-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-amine

https://huagongshe.com/reaction/718321

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
ReactantBenzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 151348—
ReactantSodium ethoxideHCID 2723922—
Reactant2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-oneHCID 50941662—
SolventEthanolHCID 702—
Product4-Ethoxy-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-2-amineHCID 5694247554.6%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a solution of 2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one (50 mg, 0.19 mmol) and BOP (110 mg, 0.25 mmol) in EtOH (1 ml) was added DBU (43 μl, 0.29 mmol). The resulting mixture was heated at 60° C. for 4 hours. After cooling down to room temperature, sodium ethoxide (26 mg, 0.38 mmol) was added. The mixture was again heated at 60° C. overnight. The solvents were removed under reduced pressure and the crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 60:1) yielding the title compound as a white solid (30 mg, 54%). mp 142° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09193741B2
Source datasetuspto-grants-2015_11
ORD IDord-7bd3ffe2af8b43b781754f24db81e09d
Source noteuspto-grants-2015_11