Reaktion #216202

Reaktionsgleichung

Na2CO3

methyl(4-(4-bromobenzylamino)-2,6-dimethylpyrimidin-5-yl)ketone

2-[(1-tert-butyl)-1H-tetrazol-5-yl]phenylboronic acid

→

product

Ausbeute 75.1%

Methyl[2,6-dimethyl-4-[(2'-(1-tert-butyl- 1H-tetrazol-5-yl)biphenyl-4-ylmethyl)amino]pyrimidin-5-yl]ketone

Ausbeute 75.1%

Lösungsmittel

EtOAc

water

EtOH

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   TemperaturHeating
3. 3
   Sonstigethe layers were separated
4. 4
   WaschenThe organic phase was washed with 0.1N NaOH, brine, dried MgSO4) and
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification by flash chromatography (40-50% EtOAc/hexane) and trituration with hexane

Vorschrift

To a heated solution of methyl(4-(4-bromobenzylamino)-2,6-dimethylpyrimidin-5-yl)ketone (1.67 g, 5.00 mmol) and tetrakis(triphenylphosphine) palladium(0) (0.29 g, 0.25 mmol) in toluene (20 mL) was added a partial solution of 2-[(1-tert-butyl)-1H-tetrazol-5-yl]phenylboronic acid (1.50 g, 6.10 mmol) (prepared according to J. W. Ellingboe, et al. U.S. Pat. No. 5,149,699) and Na2CO3 (1.06 g, 10.00 mmol) in water (10 mL) and EtOH (5 mL) in several portions over 1 h. Heating was continued for 2.5 h. The mixture was diluted with EtOAc and the layers were separated. The organic phase was washed with 0.1N NaOH, brine, dried MgSO4) and concentrated. Purification by flash chromatography (40-50% EtOAc/hexane) and trituration with hexane gave 1.71 g (75% ) of product as a white solid. An analytical sample was recrystallized from ether, mp 131°-132° C.

Quelle