Triethylamine → tert-Butyl [(6-cyano-2-pyrimidinyl)amino]acetate

HRID 748382Notes

Reaction equation

HRID 748382 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[C:4]([C:8]#[N:9])[N:3]=1.Cl.[C:11]([O:15][C:16](=[O:19])[CH2:17][NH2:18])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C.C(OCC)(=O)C>CN(C=O)C.O>[C:8]([C:4]1[N:3]=[C:2]([NH:18][CH2:17][C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:19])[N:7]=[CH:6][CH:5]=1)#[N:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 2466472-Chloropyrimidine-4-carbonitrileHCID 2725036Glycine tert-butyl ester hydrochloride

Product 1

HCID 70859670tert-Butyl [(6-cyano-2-pyrimidinyl)amino]acetateYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-Chloro-6-cyanopyrimidine (2.09 g, 15.0 mmol), glycine tert-butyl ester hydrochloride salt (2.52 g, 15.0 mmol) and triethylamine (2.38 ml, 17.0 mmol) were dissolved in DMF (30 ml), and the mixture was stirred at room temperature for 18 hrs. The reaction mixture was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the titled compound (1.07 g, 45%) as pale yellow crystals.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a9ce66d33503474a89b5893849b4eefb
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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