Diethyl Ether → Tert-butyl 2-(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)acetate

https://huagongshe.com/reaction/219265

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Diethyl Ether	HCID 3283	—
Edukt	6-Bromo-3-methyl-3,4-dihydroquinazolin-4-one	HCID 4216977	—
Edukt	HCID 178451183	HCID 178451183	—
Katalysator	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Katalysator	Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene	HCID 129828017	—
Lösungsmittel	Tetrahydrofuran	HCID 8028	—
Produkt	Tert-butyl 2-(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)acetate	HCID 57690984	—

Reaktionsbedingungen

Temperatur	50 °C

Reaktionsschritte

To a solution of 6-bromo-3-methylquinazolin-4(3H)-one (0.485 g, 2.0 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.19 g, 0.20 mmol) and Q-phos (0.20 g) in 40 mL of THF was added 2-tert-butoxy-2-oxoethylzinc chloride 0.5 M in diethyl ether (8.1 ml, 4.1 mmol). The reaction was heated at 50° C. for 16 hours and was quenched with 40 mL of satd. NH4Cl. The mixture was diluted with 60 mL of EtOAc. The organic phase was separated, washed with brine, dried over Na2SO4 and concentrated in vacuo to give red solid. The residue was purified by a silica gel column chromatography (5% EtOAc/Hex to EtOAC) to provide a red solid. MS (ESI pos. ion) m/z: 275 (MH+). Calc'd exact mass for C15H18N2O3: 274.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08198448B2
Quelldatensatz	uspto-grants-2012_06
ORD ID	ord-adc4f2dfe3fe4a29b4481d89d5aacbb5
Quellennotiz	uspto-grants-2012_06