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

HRID 499560Notes

Reaction equation

HRID 499560 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:20])[CH2:17][NH:18][CH3:19])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C.CN(C=O)C>O.C(OCC)(=O)C>[CH3:19][N:18]([CH2:17][C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:20])[C:2]1[N:7]=[CH:6][CH:5]=[C:4]([C:8]#[N:9])[N:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2466472-Chloropyrimidine-4-carbonitrileHCID 11252350Sarcosine t-butyl ester hydrochloride

Product 1

HCID 70859672tert-Butyl [methyl(6-cyano-2-pyrimidinyl)amino]acetateYield 77.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-6-cyanopyrimidine (1.45 g, 10.4 mmol), sarcosine tert-butyl ester hydrochloric acid (1.89 g, 10.4 mmol) and triethylamine (1.60 ml, 11.4 mmol) were added to 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 (1.99 g, 77%) 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-7d38f98f1a3046f1ac88d53d3311bdd0
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…