Reaktion #359841

Reaktionsgleichung

ethyl 2-(3-bromo-4-fluorophenyl)-2-hydroxyethanimidoate Hydrochloride

1,3-diaminopropane

→

title compound

Ausbeute 64.2%

1-(3-Bromo-4-fluorophenyl)-1-(2-tetrahydropyrimidinyl)methanol

Ausbeute 64.2%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to room temperature
2. 2
   Einengenconcentrated
3. 3
   Sonstigeto remove the solvent
4. 4
   workup.ADDITIONdiluted with water
5. 5
   Filtrationfiltered
6. 6
   TemperaturThe filtrate is cooled with an ice bath
7. 7
   Temperaturcooled for 1 h in an ice bath
8. 8
   Filtrationfiltered
9. 9
   SonstigeThe filtercake is dried

Vorschrift

A mixture of ethyl 2-(3-bromo-4-fluorophenyl)-2-hydroxyethanimidoate Hydrochloride (39.8 g, 127 mmol) and 1,3-diaminopropane (9.43 g, 127 mmol) in ethanol is heated at 120° C. in a sealed tube overnight, cooled to room temperature, concentrated to remove the solvent, diluted with water, stirred vigorously for 1 h and filtered. The filtrate is cooled with an ice bath, made strongly basic with 1 N NaOH, cooled for 1 h in an ice bath and filtered. The filtercake is dried to afford th title compound as a white solid 23.4 g (64% yield), identified by NMR and mass spectral analyses. 1H NMR (500 MHz, CDCl3) δ 7.59 (m, 1H), 7.30 (m, 1H), 7.10 (t, J=8.4 Hz, 1H), 4.79 (s, 1H), 3.35 (m, 4H), 1.76 (m, 2H); ESI MS m/z 287 [C11H12BrFN2O+H]+.

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