Nitrogen → 4-(Methylthio)-7-((trimethylsilyl)ethynyl)thieno[3,2-d]pyrimidine

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	Dicyclohexylamine	HCID 7582	—
Reactant	Trimethylsilylacetylene	HCID 66111	—
Reactant	7-Bromo-4-methylsulfanylthieno[3,2-d]pyrimidine	HCID 46928427	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Acetonitrile	HCID 6342	—
Product	4-(Methylthio)-7-((trimethylsilyl)ethynyl)thieno[3,2-d]pyrimidine	HCID 67327439	65.6%

Reaction Conditions

Temperature	80 °C

Reaction Steps

7-Bromo-4-(methylthio)thieno[3,2-d]pyrimidine (3 g, 11.49 mmol) was dissolved in acetonitrile (30 mL) and then bis(triphenylphosphine)palladium(II) dichloride (204 mg, 0.29 mmol), CuI (76 mg, 0.40 mmol), dicyclohexylamine (2.5 mL, 12.64 mmol) and ethynyltrimethylsilane (3.2 mL, 22.98 mmol) were added thereto. The reaction mixture was treated with N2 gas for 15 minutes and stirred at 80° C. for 14 hours. The reaction mixture was cooled to room temperature, filtered using Celite and washed with ethyl acetate (50 mL). The filtrate was washed with brine and concentrated by drying with MgSO4. The resulting mixture was purified by silica gel chromatography (ethyl acetate/hexane=1:9˜2:8) to obtain the title compound (2.1 g, 65% yield) as a yellowish solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08999973B2
Source dataset	uspto-grants-2015_04
ORD ID	ord-a36e33a791074d14a69a0490b9d346bd
Source note	uspto-grants-2015_04