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

Participants

Role	Name	HCID	Charge
Reactant	Diethyl Ether	HCID 3283	—
Reactant	6-Bromo-3-methyl-3,4-dihydroquinazolin-4-one	HCID 4216977	—
Reactant	HCID 178451183	HCID 178451183	—
Catalyst	Bis(dibenzylideneacetone)palladium	HCID 9811564	—
Catalyst	Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene	HCID 129828017	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Tert-butyl 2-(3-methyl-4-oxo-3,4-dihydroquinazolin-6-yl)acetate	HCID 57690984	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09066954B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-eeaa5f0234d94fc4a5aab9e054eb125a
Source note	uspto-grants-2015_06