Water → 2-chloro-N-(4-fluorophenyl)-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	4-Fluoroaniline	HCID 9731	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine	HCID 57990293	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-chloro-N-(4-fluorophenyl)-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine	HCID 57990415	76.2%

Reaction Conditions

Temperature	110 °C

Reaction Steps

A mixture of 2,4-dichloro-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine (260 mg, 0.556 mmol), 4-fluoroaniline (0.055 mL, 0.581 mmol) and DIEA (0.300 mL, 1.72 mmol) in dioxane (4 mL) was stirred at 110° C. for 20 h. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, then with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 2-chloro-N-(4-fluorophenyl)-5-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (230 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09139581B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-fc6313cdb2cb45f5b7c3a4c89deb918e
Source note	uspto-grants-2015_09