Phosphoric Acid → HCID 15279442, compound

HRID 1955995Notes

Reaction equation

HRID 1955995 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].C[C:10]1(C)[O:15][C:14]2[CH:16]=[CH:17][CH:18]=[C:19]([C:20]#[C:21][Si](C)(C)C)[C:13]=2[C:12](=[O:26])O1.[CH3:28][O:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[N:33]=C(S(C)(=O)=O)[N:31]=1.P(=O)(O)(O)O>O.CN(C)C=O>[CH3:28][O:29][C:30]1[CH:35]=[C:34]([O:36][CH3:37])[N:33]=[C:10]([O:15][C:14]2[CH:16]=[CH:17][CH:18]=[C:19]([C:20]#[CH:21])[C:13]=2[C:12]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])=[O:26])[N:31]=1

Participants

8

Reactant 5

HCID 1004Phosphoric AcidHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 15279441HCID 15279441, compound

Product 1

HCID 15279442HCID 15279442, compoundYield 17.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2.0 g of 2,2,2-trifluoroethanol are introduced into 80 ml of dimethylformamide and 0.60 g of 80% strength sodium hydride is added at room temperature. After 1 h, a clear solution has formed and 5.0 g of 2,2-dimethyl-5-trimethylsilylethynyl-4H-(1,3)benzodioxin-4-one are added at room temperature. After 20 min, 4.0 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine are added and the reaction solution is stirred overnight at room temperature. It is then poured into 400 ml of water containing phosphoric acid (pH 3) at 0° C. and extracted with methyl tert-butyl ether, and the combined organic phases are washed with water, dried over sodium sulfate and concentrated. 6.4 g of crude product remain, which is chromatographed on silica gel using n-hexane/ethyl acetate. A colorless oil (1.2 g) is obtained. 1H-NMR (CDCl3): δ=3.33 (s); 3.83 (s); 4.55 (q); 5.80 (s); 7.25-7.50 (m).

Workup

  1. additionis added at room temperature
  2. customa clear solution has formed
  3. waitAfter 20 min
  4. extractionextracted with methyl tert-butyl ether
  5. washthe combined organic phases are washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customwhich is chromatographed on silica gel

Sources & evidence

ORD record
ord-86f65d22f7bf4668a79f8f5287c6fbc3
Source dataset
uspto-grants-1998_07
Patent number
US05777118

Reaction notes

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