Reaction #162191

Reaction equation

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

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

ethyl 2-triphenylphosphoranylideneacetate

→

62a

Yield 99.8%

(S)-ethyl 2-(3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexylidene)ethanoate

Yield 99.8%

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureThe reaction was refluxed overnight
2. 2
   Concentrationthen concentrated in vacuo
3. 3
   Otherpurified by silica gel chromatography (Hexanes:EtOAc)
4. 4
   WashThe desired product eluted at 15% ethyl acetate
5. 5
   Concentrationconcentrated

Procedure

To a solution of (3S)-3-[(2-chloro-5-fluoro-pyrimidin-4-yl)amino]cyclohexanone (29b) (2.00 g, 8.21 mmol) in toluene (40 mL) was added ethyl 2-triphenylphosphoranylideneacetate (4.29 g, 12.31 mmol). The reaction was refluxed overnight then concentrated in vacuo and purified by silica gel chromatography (Hexanes:EtOAc). The desired product eluted at 15% ethyl acetate. Clean fractions were combined and concentrated to give 2.57 g of 62a. LCMS+: 314.18 at 3.75 min (10-90% MeOH, 3/5 grad/run, Formic Acid).

Source