Triphenylphosphine → 6-Methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,4-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	ethyl N-ethoxycarbonyliminocarbamate	HCID 220568	—
Reactant	1H-1,2,4-Triazole-1-ethanol	HCID 550925	—
Reactant	(7-Hydroxy-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate	HCID 10804576	—
Product	6-Methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,4-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one	HCID 22625017	74%

Reaction Conditions

Temperature	5 °C

Reaction Steps

The starting material was prepared as follows Diethyl azodicarboxylate (1.1 ml, 7 mmol) was added dropwise to a solution of 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one-(1.7 g, 5.55 mmol), 2-(1,2,4-triazol-1-yl)ethanol (791 mg, 7 mmol), (Ann. Pharm. Fr. 1977,35,503-508) and triphenylphosphine (1.8 g, 7 mmol) cooled at 5° C. The mixture was allowed to warm to ambient temperature and stirred for 1 hour. The mixture was poured directly on to a column of silica and eluted with methylene chloride/methanol (95/5) to give 6-methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,4-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one (1.64 g, 74%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06362336B1
Source dataset	uspto-grants-2002_03
ORD ID	ord-87054282d8d44be6a71e3670d4a11227
Source note	uspto-grants-2002_03