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

HRID 18102Notes

Reaction equation

HRID 18102 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[CH:17]=[N:18][C:19](Cl)=[N:20][CH:21]=1.C(=O)([O-])[O-:24].[K+].[K+].C(N(C(C)C)CC)(C)C>C1(C)C(C)=CC=CC=1>[C:6](=[O:7])([OH:24])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2].[Br:15][C:16]1[CH:17]=[N:18][C:19]([NH:14][CH2:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:6]([OH:5])=[O:7])=[N:20][CH:21]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 86593681(S)2-[(5-Bromo-pyrimidin-2-ylamino)-methyl]-pyrrolidin-1-carboxylic acid tert butyl carbonateYield 85%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

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

Workup

  1. temperaturewarmed
  2. temperatureto reflux for 20 h
  3. filtrationfiltered
  4. customsolvent removed at reduced pressure
  5. customchromatographed (silica gel, pentane-25% ethyl acetate/pentane)
  6. customThe appropriate fractions were collected
  7. customsolvent removed at reduced pressure

Sources & evidence

ORD record
ord-2bdfc3f175964d7eb5c13d543d883d16
Source dataset
uspto-grants-2010_06
Patent number
US07741329B2

Reaction notes

Loading…