Réaction #162192

Équation de réaction

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

62a

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

nitromethane

1,1,3,3-tetramethylguanidine

→

62b

Ethyl 2-((3S)-3-(2-chloro-5-fluoropyrimidin-4-ylamino)-1-(nitromethyl)cyclohexyl)ethanoate

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was refluxed overnight
2. 2
   Concentrationthen concentrated in vacuo
3. 3
   Autrepurified by silica gel chromatography (Hexanes:EtOAc)
4. 4
   workup.ADDITIONFractions containing pure product
5. 5
   Concentrationconcentrated

Mode opératoire

To a solution of (5)-ethyl 2-(3-(2-chloro-5-fluoropyrimidin-4-ylamino)cyclohexylidene)ethanoate, 62a, (2.58 g, 8.22 mmol) in nitromethane (44.53 mL, 822.3 mmol) was added 1,1,3,3-tetramethylguanidine (1.55 mL, 12.33 mmol). The reaction was refluxed overnight then concentrated in vacuo and purified by silica gel chromatography (Hexanes:EtOAc) then a second chromatography (CH2Cl2:20% MeOH in CH2Cl2). Fractions containing pure product were combined and concentrated to give 1.8 g of 62b

Source