Potassium Carbonate → (S)-2-[(5-Chloro-pyrimidin-2-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2074405Notes

Reaction equation

HRID 2074405 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].Cl[C:16]1[N:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].C(N(C(C)C)CC)(C)C>C1(C)C(C)=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:16]1[N:21]=[CH:20][C:19]([Cl:22])=[CH:18][N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 5906412,5-DichloropyrimidineHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylate

Product 1

HCID 67090501(S)-2-[(5-Chloro-pyrimidin-2-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl esterYield 48.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

(S)-2-Aminomethyl pyrrolidine-1-carboxylic acid tert-butyl ester (3.38 g), 2,5-dichloropyrimidine (2.50 g), potassium carbonate (4.67 g) and diisopropylethylamine (8.79 ml) were heated in xylene (60 ml) at 100° C. for 3.75 h. The cooled reaction mixture was filtered and the filtrate evaporated to a gum which was chromatographed on silica gel, eluting with ethyl acetate-pentane fractions, to afford the title compound as a pale yellow solid (2.55 g). Mass Spectrum (API+): Found 213 (MH+−tBoc). C14H2135ClN4O2 requires 312.

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. customthe filtrate evaporated to a gum which
  4. customwas chromatographed on silica gel
  5. washeluting with ethyl acetate-pentane fractions

Sources & evidence

ORD record
ord-2f6cbe94d1734b70af3d2087d6da4ab7
Source dataset
uspto-grants-2011_04
Patent number
US07919507B2

Reaction notes

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