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

HRID 2074402Notes

Reaction equation

HRID 2074402 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-7a1942cbffeb46d9b6d22bbce1502324
Source dataset
uspto-grants-2011_04
Patent number
US07919507B2

Reaction notes

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