Phosphorus oxychloride → HCID 136011334, compound

HRID 2183583Notes

Reaction equation

HRID 2183583 reaction equation
O[C:2]1[C:3]2[CH:16]=[N:15][N:14]([CH3:17])[C:4]=2[NH:5][C:6](=[O:13])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].P(Cl)(Cl)([Cl:20])=O>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:20][C:2]1[C:3]2[CH:16]=[N:15][N:14]([CH3:17])[C:4]=2[NH:5][C:6](=[O:13])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135713177HCID 135713177, compound

Product 1

HCID 136011334HCID 136011334, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A solution of ethyl 4-hydroxy-1-methyl-6-oxo-6,7-dihyrdo-1H-pyrazolo-[3,4-b]pyridine-5-carboxylate (10 g, 42.2 mmol) in acetonitrile is treated with benzyl triethyl ammonium chloride (40.4 g, 169 mmol), followed by phosphorous oxychloride (17.6 mL, 190 mmol), heated at 40° C. for 0.5 h, then at reflux temperature for 2.5 h, cooled to room temperature, diluted with water (caution exotherm), stirred at ambient temperatures for 16 h and filtered. The filtercake is washed with cyclohexane and dried in vacuo to give the title compound as a white solid, 7.87 g (73% yield), identified by HNMR analysis.

Workup

  1. temperatureat reflux temperature for 2.5 h
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. washThe filtercake is washed with cyclohexane
  5. customdried in vacuo

Sources & evidence

ORD record
ord-297aa9f68649467799a850d9ee36dd2a
Source dataset
uspto-grants-2005_05
Patent number
US06900223B2

Reaction notes

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