Reaction #46380

Reaction equation

(S)-2-Aminomethyl-pyrrolidine-1-carboxylic acid tert butyl ester

5-bromo-2-chloropyrimidine

potassium carbonate

diisopropylethylamine

→

title compound

Yield 85.0%

(S)2-[(5-Bromo-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-carboxylic acid tert butyl carbonate

Yield 85.0%

Solvents

xylene

Conditions

Workup

1. 1
   Temperaturewarmed
2. 2
   Temperatureto reflux for 20 h
3. 3
   Filtrationfiltered
4. 4
   Othersolvent removed at reduced pressure
5. 5
   Otherchromatographed (silica gel, pentane-25% ethyl acetate/pentane)
6. 6
   OtherThe appropriate fractions were collected
7. 7
   Othersolvent removed at reduced pressure

Procedure

(S)-2-Aminomethyl-pyrrolidine-1-carboxylic acid tert butyl ester (2 g), 5-bromo-2-chloropyrimidine (1.93 g) were combined in xylene (40 ml) containing potassium carbonate (2.76 g) and diisopropylethylamine (5.23 ml) and warmed to reflux for 20 h. The mixture was cooled to room temperature, filtered and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, pentane-25% ethyl acetate/pentane). The appropriate fractions were collected, solvent removed at reduced pressure to give the title compound (1.78 g) as a colourless gum

Source