Réaction #162189

Équation de réaction

(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

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Extractionextracted twice with EtOAc
2. 2
   LavageThe combined organic phases were washed twice with brine
3. 3
   Séchagedried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe crude residue was purified by silica gel chromatography

Mode opératoire

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.

Source