Water → 2-chloro-N-cyclopropyl-7-tosyl-5-vinyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Tetravinylstannane	HCID 66189	—
Reactant	2-chloro-N-cyclopropyl-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine	HCID 57990325	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-chloro-N-cyclopropyl-7-tosyl-5-vinyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine	HCID 57990341	25.8%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A solution of 2-chloro-N-cyclopropyl-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (190 mg, 0.389 mmol) in dioxane (3 mL) was degassed with Ar before being charged with tetravinyltin (0.105 mL, 0.576 mmol) and Pd(Ph3P)4 (41 mg, 0.035 mmol). The mixture was stirred at 100° C. for 3 h. Water and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give 2-chloro-N-cyclopropyl-7-tosyl-5-vinyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (39 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08258144B2
Source dataset	uspto-grants-2012_09
ORD ID	ord-1e70d675f9d14da3b5c53bc62d60a41b
Source note	uspto-grants-2012_09