Triethylamine → [2-Chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]-(1-ethyl-propyl)-amine

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	3,3-Diethoxypropyne	HCID 66285	—
Reactant	5-bromo-2-chloro-N-(pentan-3-yl)pyrimidin-4-amine	HCID 58015891	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[2-Chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]-(1-ethyl-propyl)-amine	HCID 58015829	37.2%

Reaction Conditions

Temperature	55 °C

Reaction Steps

To a mixture of (5-bromo-2-chloro-pyrimidin-4-yl)-(1-ethyl-propyl)-amine (420 mg, 1.5 mmol) and propargylaldehyde diethyl acetal (0.32 mL, 2.25 mmol) in DMF (6 mL) is added PdCl2(PPh3)2 (105 mg, 0.15 mmol) and CuI (28 mg, 0.15 mmol), followed by Et3N (0.42 mL, 3 mmol). The mixture is degassed, and heated at 55° C. for 16 h. After cooling to room temperature, the reaction mixture is diluted with EtOAc, washed with water and brine. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product is purified by column chromatography (SiO2, EtOAc/heptane 5:95 to 40:60) to give 182 mg of [2-chloro-5-(3,3-diethoxy-prop-1-ynyl)-pyrimidin-4-yl]-(1-ethyl-propyl)-amine as a light brown oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08324225B2
Source dataset	uspto-grants-2012_12
ORD ID	ord-13ef3f81f0454bf48df3def08ce1aa9f
Source note	uspto-grants-2012_12