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

HRID 2113533Notes

Reaction equation

HRID 2113533 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-d56ec55fba0047aab3228ef773e54ede
Source dataset
uspto-grants-2008_10
Patent number
US07432270B2

Reaction notes

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