Diisopropylethylamine → 4-chloro-6-(1-trimethylsilanylmethyl-1H-[1,2,3]triazol-4-yl)-thieno[3,2-d]pyrimidine

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Trimethylsilylmethyl Azide	HCID 150751	—
Reactant	4-Chloro-6-ethynylthieno[3,2-d]pyrimidine	HCID 59982262	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-chloro-6-(1-trimethylsilanylmethyl-1H-[1,2,3]triazol-4-yl)-thieno[3,2-d]pyrimidine	HCID 86603174	—

Reaction Steps

A mixture of compound 48.2 (1.0 mmol), trimethylsilylmethyl azide (5.0 mmol), CuI (0.2 mmol), and DIEA (1.0 mmol) in DMF (10 mL) was stirred at room temperature for 24 hours. The solvent was removed and the residue was diluted with water and extracted with EtOAc. The organic layer was washed with dilute aqueous ammonium hydroxide, brine, dried, concentrated and purified by flash column chromatography to provide 4-chloro-6-(1-trimethylsilanylmethyl-1H-[1,2,3]triazol-4-yl)-thieno[3,2-d]pyrimidine (compound 48.3) in 80% yield. EIMS (m/z): calcd. for C12H14ClN5SSi (M+)+H 324.04. found 324.00.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07601725B2
Source dataset	uspto-grants-2009_10
ORD ID	ord-8b26ec62de9b49de941f348354d2e8d4
Source note	uspto-grants-2009_10