Chlorotrimethylsilane → N-(4-(4-(2-aminoethylamino)-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-(2-aminoethyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-amine	HCID 86636619	—
Solvent	1-Butanol	HCID 263	—
Product	N-(4-(4-(2-aminoethylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide	HCID 57990364	24.3%

Reaction Conditions

Temperature	116 °C

Reaction Steps

A mixture of N-(2-aminoethyl)-2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-amine (71 mg, 0.34 mmol), N-(4-aminophenyl)-N-methylacetamide (110 mg, 0.67 mmol) and trimethylsilyl chloride (0.085 mL, 0.67 mmol) in nBuOH (2 mL) was heated at 116° C. for 3 h. More trimethylsilyl chloride (0.100 mL, 0.79 mmol) was added. After being stirred at 116° C. for another 2 h, the mixture was purified by HPLC to give the titled compound (28 mg). MS 340.2 (M+H); UV 201.4, 262.7, 303.1 nm.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09139581B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-85d91752eb15422d827ed1d56b73d441
Source note	uspto-grants-2015_09