1,10-Phenanthroline → 3-(3-Oxo-4-pyrimidin-2-yl-piperazin-1-yl)-azetidine-1-carboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	1,10-Phenanthroline	HCID 1318	—
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	2-Bromopyrimidine	HCID 78345	—
Reactant	1-Boc-3-(3-oxo-1-piperazinyl)azetidine	HCID 59605439	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Toluene	HCID 1140	—
Solvent	Dichloromethane	HCID 6344	—
Product	3-(3-Oxo-4-pyrimidin-2-yl-piperazin-1-yl)-azetidine-1-carboxylic acid tert-butyl ester	HCID 66836249	36.8%

Reaction Conditions

Temperature	110 °C

Reaction Steps

A mixture of intermediate 4b (52 mg, 0.204 mmol), 2-bromopyrimidine 1i (65 mg, 0.41 mmol), CuI (8 mg, 0.04 mmol), 1,10-phenanthroline (18 mg, 0.10 mmol), and K3PO4 (95 mg, 0.45 mmol) in toluene (1 mL) was heated at 110° C. under N2 for 9 h. The reaction mixture was diluted with CH2Cl2 and filtered. The solution was concentrated and purification by column chromatography (silica gel, 3% MeOH/CH2Cl2) gave intermediate 3c as light yellow solid (25 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08637498B2
Source dataset	uspto-grants-2014_01
ORD ID	ord-68440521ea3d43a188786ef8be7d78a5
Source note	uspto-grants-2014_01