Acetic Anhydride → 8-ethyl-6-(1H-imidazol-5-yl)-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1666272Notes

Reaction equation

HRID 1666272 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]2[NH:27][CH:26]=[N:25][CH:24]=2)[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]2[NH:27][CH:26]=[N:25][CH:24]=2)[C:11]1=[O:3])[CH3:9]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 576069688-ethyl-6-(1H-imidazol-5-yl)-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-imine

Product 1

HCID 576069708-ethyl-6-(1H-imidazol-5-yl)-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Conditions

Temperature
100 °C

Procedure

Acetic anhydride (15.0 mL) was added to a flask charged with crude 8-ethyl-6-(1H-imidazol-5-yl)-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-imine and heated to 100° C. After 30 minutes, the reaction was allowed to cool to room temperature and concentrated in vacuo. The acetylated residue was then treated with 6 N HCl (16 mL) and heated to 95° C. for 30 minutes then transferred to a large flask. A saturated solution of NaHCO3 (150 mL) was added at 0° C. to about pH=8.0. 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 off and the organic layers were concentrated in vacuo to afford crude 8-ethyl-6-(1H-imidazol-5-yl)-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one 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 (16 mL)
  4. temperatureheated to 95° C. for 30 minutes
  5. customthen transferred to a large flask
  6. additionA saturated solution of NaHCO3 (150 mL) was added at 0° C. to about 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 off
  11. concentrationthe organic layers were concentrated in vacuo

Sources & evidence

ORD record
ord-af6fa52694044da7a2ea25068c806a96
Source dataset
uspto-grants-2011_10
Patent number
US08044062B2

Reaction notes

Loading…