Chlorotrimethylsilane → N-(4-(4-(cyclopropylamino)-5-(pyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide

Participants

Role	Name	HCID	Charge
Reactant	Chlorotrimethylsilane	HCID 6397	—
Reactant	N-(4-Aminophenyl)-N-methylacetamide	HCID 67068	—
Reactant	2-chloro-N-cyclopropyl-5-(pyridin-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine	HCID 57990302	—
Solvent	1-Butanol	HCID 263	—
Product	N-(4-(4-(cyclopropylamino)-5-(pyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide	HCID 57990353	31.8%

Reaction Conditions

Temperature	135 °C

Reaction Steps

A mixture of 2-chloro-N-cyclopropyl-5-(pyridin-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (85 mg, 0.19 mmol), N-(4-aminophenyl)-N-methylacetamide (72 mg, 0.44 mmol) and TMSCl (0.100 mL, 0.79 mmol) in nBuOH (3 mL) was stirred at 135° C. for 18 h. It was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (25 mg). MS 414.3 (M+H); UV 202.8, 280.8 nm.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08258144B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-5723575787b64416b72332222e973124
Source note	uspto-grants-2012_09