Dimethylformamide → HCID 58170006, compound

HRID 444825Notes

Reaction equation

HRID 444825 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:10][C:11](=[O:20])[C:12]2[N:13]([N:15]=[C:16]([CH2:18][OH:19])[CH:17]=2)[CH:14]=1.COCCOC.CN(C=O)C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[NH:10][C:11](=[O:20])[C:12]2[N:13]([N:15]=[C:16]([CH:18]=[O:19])[CH:17]=2)[CH:14]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 80711,2-DimethoxyethaneHCID 159087TriacetoxyperiodinaneHCID 58170050HCID 58170050, compound

Product 1

HCID 58170006HCID 58170006, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.15 g (3.37 mmol) of 6-(2,4-dichlorophenyl)-2-(hydroxymethyl)pyrazolo[1,5-a]pyrazin-4(5H)-one (Example 17A) were suspended in 100 ml of dichloromethane, and 1 drop of water was added. 100 ml of 1,2-dimethoxyethane and 9.6 ml of DMF were then added, and the mixture was cooled to 0° C. 7.16 g (16.87 mmol) of Dess-Martin periodinane were added, ice-bath cooling was removed and the mixture was stirred at RT for 15 h. Ethyl acetate and then 200 ml of a 10% strength sodium thiosulfate solution were added to the mixture, and the organic phase was washed with saturated aqueous sodium bicarbonate solution. Drying of the organic phase with sodium sulfate and removal of the solvent under reduced pressure gave 660 mg (57% of theory) of the product as a solid which was reacted without any further purification.

Workup

  1. temperatureice-bath cooling
  2. customwas removed
  3. additionEthyl acetate and then 200 ml of a 10% strength sodium thiosulfate solution were added to the mixture
  4. washthe organic phase was washed with saturated aqueous sodium bicarbonate solution
  5. dry with materialDrying of the organic phase with sodium sulfate and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-0d0e718c707f4a268c3b338efd478c42
Source dataset
uspto-grants-2013_07
Patent number
US08476267B2

Reaction notes

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