Sodium Hydroxide → HCID 59757322, compound

HRID 1510822Notes

Reaction equation

HRID 1510822 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[C:16]([O:18]C)=[O:17])=[C:12]([CH:20]([CH3:22])[CH3:21])[N:11]=[C:10]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])=[C:12]([CH:20]([CH3:21])[CH3:22])[N:11]=[C:10]([N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68545130HCID 68545130, compound

Product 1

HCID 59757322HCID 59757322, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of methyl 3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl](2E)-propenoate (10 g) in ethanol (200 ml) was treated with aqueous sodium hydroxide solution (0.1N, 246 ml) at 0-5° C. The reaction mixture was stirred at 25-30° C. for 12 h for completion of hydrolysis and ethanol was evaporated under reduced pressure. The resulting mass was acidified and extracted with methylene chloride (2×100 ml). The organic layer was washed with water, dried and concentrated to give the title product (Yield 9.4 g).

Workup

  1. customwas evaporated under reduced pressure
  2. extractionextracted with methylene chloride (2×100 ml)
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-648e8709497746abbe8fbaf0e7627839
Source dataset
uspto-grants-2012_07
Patent number
US08212034B2

Reaction notes

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