4-Fluoroiodobenzene → N-Butyl-5-(4-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-amine

https://huagongshe.com/reaction/920663

Participants

Role	Name	HCID	Charge
Reactant	4-Fluoroiodobenzene	HCID 9605	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	1-N,2-N-dimethylcyclohexane-1,2-diamine	HCID 551074	—
Reactant	N-Butyl-5H-pyrrolo[3,2-d]pyrimidin-2-amine	HCID 86731154	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	N-Butyl-5-(4-fluorophenyl)-5H-pyrrolo[3,2-d]pyrimidin-2-amine	HCID 86731155	99%

Reaction Conditions

Temperature	110 °C

Reaction Steps

A mixture of N-butyl-5H-pyrrolo[3,2-d]pyrimidin-2-amine (0.73 g, 3.85 mmol), CuI (0.074 g, 0.39 mmol), and K3PO4 (1.63 g, 7.7 mmol) was added DMF (10 mL), 4-fluoroiodobenzene (0.54 mL, 4.62 mmol), and N,N′-dimethylcyclohexane-1,2-diamine (0.24 mL, 1.54 mmol) under Argon atmosphere. The mixture was heated at 110° C. for 16 h, then was filtered through a plug of celite at room temperature and washed with MeOH. The filtrate was concentrated and purified by ISCO to provide desired product (1.079 g, 99%). MS m/z 285.2 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09273056B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-7684b0d758e24374ab826433625f81e7
Source note	uspto-grants-2016_03