Water → 1-(4-(4-(4-(methylthio)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Chlorotrimethylsilane	HCID 6397	—
Reactant	1-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-one	HCID 736269	—
Reactant	2-chloro-4-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine	HCID 57990275	—
Solvent	1-Butanol	HCID 263	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	1-(4-(4-(4-(methylthio)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone	HCID 69023137	48.7%

Reaction Conditions

Temperature	116 °C

Reaction Steps

A mixture of 2-chloro-4-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine (484 mg, 2.43 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (645 mg, 2.95 mmol) and trimethylsilyl chloride (0.500 mL, 3.95 mmol) in nBuOH (10 mL) was heated at 116° C. for 48 h. After cooling down, H2O and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 1-(4-(4-(4-(methylthio)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone as a solid (453 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09139581B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-3a5a9ffb2f4749749d9b38f9ce9ab9e9
Source note	uspto-grants-2015_09