Diethyl Ether → Tert-butyl 2-(4-aminoquinazolin-6-yl)acetate

Participants

Role	Name	HCID	Charge
Reactant	Diethyl Ether	HCID 3283	—
Reactant	6-Bromoquinazolin-4-amine	HCID 728935	—
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-(4-aminoquinazolin-6-yl)acetate	HCID 57690924	—

Reaction Conditions

Temperature	50 °C

Reaction Steps

To a solution of 6-bromoquinazolin-4-amine (0.400 g, 1.79 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.163 g, 0.179 mmol) and Q-phos (0.20 g) in 10 mL of THF was added 2-tert-butoxy-2-oxoethylzinc chloride 0.5 m in diethyl ether (10.7 ml, 5.36 mmol). The reaction was heated at 50° C. for 16 hours and was quenched with 50 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 give red solid tert-butyl 2-(4-aminoquinazolin-6-yl)acetate which was used without further purification. MS (ESI pos. ion) m/z: 260.1 (M+H). Calc'd Exact Mass for C14H17N3O2: 259.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09066954B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-f86b2033733948d58cfa795131e2c6d0
Source note	uspto-grants-2015_06