Diisopropylethylamine → 2-[4-(2-Chloro-pyrimidin-5-ylethynyl)-phenyl]-N-ethyl-propionamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Chloro-5-iodopyrimidine	HCID 1714223	—
Reactant	N-Ethyl-2-(4-ethynyl-phenyl)-propionamide	HCID 86669567	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-[4-(2-Chloro-pyrimidin-5-ylethynyl)-phenyl]-N-ethyl-propionamide	HCID 86669568	—

Reaction Steps

To 1.10 g (5.46 mmol) N-ethyl-2-(4-ethynyl-phenyl)-propionamide (XVII.1) in 10 mL THF are added 1.31 g (5.46 mmol) 2-chloro-5-iodo-pyrimidine under argon, followed by 0.42 g (0.60 mmol) Pd(PPh3)2Cl2 as catalyst, 57 mg (0.30 mmol) copper(I)iodide and 2.1 mL (12 mmol) DIPEA as base. The mixture is stirred at rt for 4 h. After that time, the mixture is filtered and the solvent is evaporated from the filtrate. The residue is purified by column chromatography (silicia gel; DCM:MeOH gradient 1:0/1:1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08877754B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-3fb5c3261f5545acbc572579b0d6e36a
Source note	uspto-grants-2014_11