Reaction #162189

Reaction equation

(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

Solvents

DMF

Conditions

Workup

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

Procedure

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