Reacción #162189

Ecuación de reacción

(3S)-3-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]cyclohexanone

29b

(S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanone

3-bromoprop-1-ene

NH4Cl

→

desired product

(3S)-1-allyl-3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexanol

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted twice with EtOAc
2. 2
   LavadoThe combined organic phases were washed twice with brine
3. 3
   Secadodried (MgSO4)
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe crude residue was purified by silica gel chromatography

Procedimiento

To a solution of (3S)-3-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]cyclohexanone, 29b, (0.60 g, 2.46 mmol) and 3-bromoprop-1-ene (0.43 mL, 4.92 mmol) in DMF was added Zn dust (0.32 g, 4.92 mmol). The reaction was stirred at room temperature for 3 days. The mixture was diluted into aqueous saturated NH4Cl solution, extracted twice with EtOAc. The combined organic phases were washed twice with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography using 0-50% EtOAc/hexanes gradient to afford 553 mg of desired product, 58a, as an oil. LC/MS-two peaks corresponding to two diastereomeric products: 286.4 (M+H), RT=3.41 and 3.78.

Fuente