Chlorotrimethylsilane → N-(4-(4-(5-aminopentylamino)-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	N-(5-aminopentyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-amine	HCID 86636620	—
Solvent	1-Butanol	HCID 263	—
Product	N-(4-(4-(5-aminopentylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide	HCID 57990326	7.6%

Reaction Conditions

Temperature	116 °C

Reaction Steps

A mixture of N-(5-aminopentyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-amine (79 mg, 0.31 mmol), N-(4-aminophenyl)-N-methylacetamide (100 mg, 0.61 mmol) and trimethylsilyl chloride (0.150 mL, 1.19 mmol) in nBuOH (2 mL) was heated at 116° C. for 4 h. The mixture was then purified by HPLC to give the titled compound (9 mg). MS 382.2 (M+H); UV 210.8, 267.5, 305.5 nm.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09139581B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-9c5aee1387e249a3a9036560a86e991d
Source note	uspto-grants-2015_09