Reaktion #68587

Reaktionsgleichung

6-bromoquinazolin-4-amine

2-tert-butoxy-2-oxoethylzinc chloride

diethyl ether

→

tert-butyl 2-(4-aminoquinazolin-6-yl)acetate

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas quenched with 50 mL of satd
2. 2
   workup.ADDITIONThe mixture was diluted with 60 mL of EtOAc
3. 3
   SonstigeThe organic phase was separated
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigeto give red solid
8. 8
   SonstigeThe residue was purified by a silica gel column chromatography (5% EtOAc/hex to EtOAC)

Vorschrift

To a solution of 6-bromoquinazolin-4-amine (0.400 g, 1.79 mmol), tris(dibenzylideneacetone)dipalladium (o) (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 C14H12N3O2: 259.1.

Quelle