Water → HCID 15766823, compound

HRID 1290616Notes

Reaction equation

HRID 1290616 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([F:14])([CH3:13])[CH:7]([OH:12])[C:8]([O:10][CH3:11])=[O:9].[H-].[Na+].[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21](S(C)(=O)=O)[N:20]=1.O>CN(C)C=O.C(O)(=O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([F:14])([CH3:13])[CH:7]([O:12][C:21]1[N:22]=[C:23]([O:25][CH3:26])[CH:24]=[C:19]([O:18][CH3:17])[N:20]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 15766822HCID 15766822, compound2×

Product 1

HCID 15766823HCID 15766823, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

2.2 g (10 mmol) of methyl 3-(2-thienyl)-3-fluoro-2-hydroxybutyrate (Compound 1.1) are dissolved in 40 ml of dimethylformamide, and 0.3 g (12 mmol) of sodium hydride is added. The mixture is stirred for 1 hour, and 2.2 g (10 mmol) of 4,6-dimethoxy-2-methylsulfonylpyrimidine are then added. After the mixture has been stirred at room temperature for 24 hours, it is hydrolyzed using 10 ml of water, the pH is brought to 5 using acetic acid, and the solvent is distilled off under a high vacuum. The residue is taken up in ethyl acetate, washed with water and dried over sodium sulfate, and the solvent is distilled off. The residue is treated with 10 ml of methyl t-butyl ether and the precipitate formed filtered off with suction. After drying, 1.8 g of a white powder remain.

Workup

  1. stirringAfter the mixture has been stirred at room temperature for 24 hours
  2. distillationthe solvent is distilled off under a high vacuum
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent is distilled off
  6. additionThe residue is treated with 10 ml of methyl t-butyl ether
  7. customthe precipitate formed
  8. filtrationfiltered off with suction
  9. customAfter drying

Sources & evidence

ORD record
ord-19a6fa1711094d2da263d384dba45c6a
Source dataset
uspto-grants-1998_05
Patent number
US05753594

Reaction notes

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