Ethanol → HCID 58296327, compound

HRID 390039Notes

Reaction equation

HRID 390039 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[N:5]=[C:4]([S:21][CH3:22])[N:3]=1.[OH-].[Na+].C(O)C>O>[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[CH:15]=2)[N:5]=[C:4]([S:21][CH3:22])[N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 58296350HCID 58296350, compound

Product 1

HCID 58296327HCID 58296327, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 ml round-bottom flask were added ethyl 4-methyl-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarboxylate (2.83 g, 8.92 mmole), sodium hydroxide (dissolved in 5 mL of water) (0.53 g, 13.4 mmole), ethanol (25 mL) and water (25 mL). The reaction was stirred at reflux for 2 h. It was cooled to room temperature and concentrated under vacuum. The residue was treated with water (100 mL) and acidified by dropwise addition of acetic acid. Ethyl acetate (500 mL) was then added and the mixture was stirred for 10 min. The organic phase was separated. The aqueous phase was extracted with ethyl acetate (2×) and the organic extracts were combined and washed with water, brine and dried over MgSO4. The solvent was removed under vacuum to yield the product (2.6 g).

Workup

  1. temperatureat reflux for 2 h
  2. concentrationconcentrated under vacuum
  3. additionThe residue was treated with water (100 mL)
  4. additionacidified by dropwise addition of acetic acid
  5. additionEthyl acetate (500 mL) was then added
  6. stirringthe mixture was stirred for 10 min
  7. customThe organic phase was separated
  8. extractionThe aqueous phase was extracted with ethyl acetate (2×)
  9. washwashed with water, brine
  10. dry with materialdried over MgSO4
  11. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-5f23d14d303b44f5a005a0a645cdfe01
Source dataset
uspto-grants-2013_02
Patent number
US08383635B2

Reaction notes

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