Acetic Anhydride → 8-Ethyl-4-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile

HRID 886809Notes

Reaction equation

HRID 886809 reaction equation
C(OC(=O)C)(=[O:3])C.[CH2:8]([N:10]1[C:15]2[N:16]=[C:17]([S:21][CH3:22])[N:18]=[C:19]([CH3:20])[C:14]=2[CH:13]=[C:12]([C:23]#[N:24])[C:11]1=N)[CH3:9]>>[CH2:8]([N:10]1[C:15]2[N:16]=[C:17]([S:21][CH3:22])[N:18]=[C:19]([CH3:20])[C:14]=2[CH:13]=[C:12]([C:23]#[N:24])[C:11]1=[O:3])[CH3:9]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 576069898-Ethyl-7-imino-4-methyl-2-(methylthio)-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile

Product 1

HCID 576069618-Ethyl-4-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions

Temperature
100 °C

Procedure

Acetic anhydride (10.0 mL) was added to a flask charged with 8-ethyl-7-imino-4-methyl-2-(methylthio)-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (0.506 g, 1.95 mmol) and heated to 100° C. After one h, the reaction was allowed to cool to room temperature and concentrated in vacuo. The acetylated residue was then treated with 6 N HCl (40 mL) and heated to 95° C. for one hour then transferred to a large flask. A saturated solution of NaHCO3 (500 mL) was added slowly at 0° C. until a ˜pH 8.0 was achieved. The aqueous phase was washed thrice with ethyl acetate (100 mL) and the organic layers combined, then washed with brine and dried over Na2SO4. The drying agent was filtered and concentrated in vacuo to afford crude 8-ethyl-4-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitrile which was used in the subsequent step without further purification.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe acetylated residue was then treated with 6 N HCl (40 mL)
  4. temperatureheated to 95° C. for one hour
  5. customthen transferred to a large flask
  6. additionA saturated solution of NaHCO3 (500 mL) was added slowly at 0° C. until a ˜pH 8.0
  7. washThe aqueous phase was washed thrice with ethyl acetate (100 mL)
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. filtrationThe drying agent was filtered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5684e3043e724482a396a303a6ce99fc
Source dataset
uspto-grants-2012_08
Patent number
US08247408B2

Reaction notes

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