p-Toluenesulfonic acid → 2-(2-(Methylthio)pyrimidin-4-yl)acetonitrile

HRID 629485Notes

Reaction equation

HRID 629485 reaction equation
C(OC(=O)[CH:7]([C:16]#[N:17])[C:8]1[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=1)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:15][S:14][C:10]1[N:9]=[C:8]([CH2:7][C:16]#[N:17])[CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 51034226Cyano-(2-methylthio-pyrimidin-4-yl)-acetic acid tert-butyl ester

Product 1

HCID 671997982-(2-(Methylthio)pyrimidin-4-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of Intermediate cyano-(2-methylthio-pyrimidin-4-yl)-acetic acid tert-butyl ester (5.3 g, 20 mmol) in anhydrous toluene (100 mL) was added p-toluenesulfonic acid (800 mg). The mixture was heated to reflux for 8 h, cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with 1N aqueous sodium hydroxide solution and brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography (3:1 hexanes/ethyl acetate eluant) to afford the title compound: 1H NMR 400 MHz (CDCl3) δ 8.56 (d, 1H), 7.12 (d, 1H), 3.84 (s, 2H), 2.57 (s, 3H); MS m/z: 166.0 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with 1N aqueous sodium hydroxide solution and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by silica gel chromatography (3:1 hexanes/ethyl acetate eluant)

Sources & evidence

ORD record
ord-ba8208fd542546c9954abedf052cb8d4
Source dataset
uspto-grants-2016_04
Patent number
US09314464B2

Reaction notes

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