Pyridine → n-(6-chloro-2-methylpyrimidin-4-yl)acetamide

HRID 1621486Notes

Reaction equation

HRID 1621486 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.N1C=CC=CC=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:16](=[O:18])[CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 2867546-Chloro-2-methylpyrimidin-4-amine

Product 1

HCID 243561n-(6-chloro-2-methylpyrimidin-4-yl)acetamideYield 71%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 6-chloro-2-methylpyrimidin-4-amine (500 mg, 3483 μmol), pyridine (568 μl, 6965 μmol), and acetic anhydride (493 μl, 5224 μmol) was stirred at 40° C. for 24 h. The mixture was cooled down to rt. The reaction mixture was diluted with saturated NaHCO3 (30 mL) and extracted with EtOAc (2×40 mL). The organic extract was washed with saturated NaCl (about 2 mL), dried over Na2SO4, filtered, concentrated in vacuo and the residue was purified by silica gel chromatography eluting with 40% EtOAc/hexanes to give N-(6-chloro-2-methylpyrimidin-4-yl)acetamide (458 mg, 71% yield). 1H NMR (300 MHz, CDCl3) δ 8.03 (s, 1H); 7.90 (s, 1H); 2.58 (s, 3H); 2.23 (s, 3H). m/z (ESI, +ve ion) 186 (M+H)+.

Workup

  1. temperatureThe mixture was cooled down to rt
  2. extractionextracted with EtOAc (2×40 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (about 2 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by silica gel chromatography
  9. washeluting with 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-0ef1930e67ac4ec98e392578aa0bf046
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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