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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2277747Generated: November 3, 2026

Cyanamide → (Rac)-[[3-({4-[2-(benzyloxy)-4-fluorophenyl]-5-fluoropyrimidin-2-yl}amino)benzyl](methyl)-lambda4-sulfanylidene]-cyanamide

https://huagongshe.com/reaction/2277747

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCyanamideHCID 9864—
ReactantN-BromophthalimideHCID 75542—
ReactantPotassium tert-butoxideHCID 23665647—
Reactant4-[2-(Benzyloxy)-4-fluorophenyl]-5-fluoro-N-{3-[(methylsulfanyl)methyl]phenyl}pyrimidin-2-amineHCID 89444601—
SolventMethanolHCID 887—
SolventDichloromethaneHCID 6344—
SolventSodium ThiosulfateHCID 24477—
Product(Rac)-[[3-({4-[2-(benzyloxy)-4-fluorophenyl]-5-fluoropyrimidin-2-yl}amino)benzyl](methyl)-lambda4-sulfanylidene]-cyanamideHCID 89444507—

Reaction Steps

2-Bromo-1H-isoindole-1,3(2H)-dione (22.0 mg; 0.12 mmol) was added to a solution of 4-[2-(benzyloxy)-4-fluorophenyl]-5-fluoro-N-{3-[(methylsulfanyl)methyl]phenyl}pyrimidin-2-amine (37.0 mg; 0.08 mmol), cyanamide (4.5 mg; 0.11 mmol) and potassium 2-methylpropan-2-olate (11.1 mg; 0.10 mmol) in MeOH (0.44 mL) at RT. The batch was stirred for 4 hours before it was diluted with DCM and aqueous sodium thiosulfate solution. The batch was extracted with DCM (2×). The combined organic phases were filtered using a Whatman filter and concentrated to give crude (rac)-[[3-({4-[2-(benzyloxy)-4-fluorophenyl]-5-fluoropyrimidin-2-yl}amino)benzyl](methyl)-λ4-sulfanylidene]-cyanamide that was used without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09133171B2
Source datasetuspto-grants-2015_09
ORD IDord-2e9f6b7f2e684585bd52bdc6bb16603e
Source noteuspto-grants-2015_09