Benzylacetylene → 2-(Methylthio)-6-benzyl-furano[2,3-d]pyrimidine

Participants

Role	Name	HCID	Charge
Reactant	Benzylacetylene	HCID 575753	—
Reactant	HCID 178418710	HCID 178418710	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Dichlorobis(triphenylphosphine)palladium	HCID 6102075	—
Solvent	Triethylamine	HCID 8471	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	2-(Methylthio)-6-benzyl-furano[2,3-d]pyrimidine	HCID 21039980	—

Reaction Conditions

Temperature	40 °C

Reaction Steps

A mixture of 2-methylthio-4-hydroxy-5-iodopyrimidine (2.65 g), 3-phenyl-1-propyne (1.49 mL), copper (I) iodide (90 mg) and bis(triphenylphosphine) Palladium (II) dichloride (Fluka, 160 mg) in 20 mL of triethylamine and NMP (7 mL) was stirred at 40° C. for 6 hours. The reaction mixture was diluted with ethyl acetate (100 mL), washed with brine (3×50 mL), concentrated and purified by column chromatography (5% EtOAc/hexanes) to give 0.57 g of a solid product. MP: 69–72.2° C. MS: 257.2 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07091347B2
Source dataset	uspto-grants-2006_08
ORD ID	ord-6762f22478744c559d8ab1ec0f6d6574
Source note	uspto-grants-2006_08