Phosphorus oxychloride → HCID 86636111, compound

HRID 1931780Notes

Reaction equation

HRID 1931780 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[N:19]=[C:20]([O:24][CH3:25])[NH:21][C:22](=O)[C:17]=3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:28])=O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][C:20]([O:24][CH3:25])=[N:21][C:22]([Cl:28])=[C:17]3[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136346604HCID 136346604, compound

Product 1

HCID 86636111HCID 86636111, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(6-methoxy-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (1 mmol), phosphorus oxychloride (2 mmol) and dimethylformamide (5 drops) is heated at 80° C. for 6 h. The mixture is allowed to cool, the solvent is evaporated and the residue is poured into ice-water. The mixture is extracted three times with ethyl acetate. The combined ethyl acetate extracts are washed with brine, dried (magnesium sulfate), filtered, and evaporated to give crude 4-(4-chloro-6-methoxy-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperatureto cool
  2. customthe solvent is evaporated
  3. additionthe residue is poured into ice-water
  4. extractionThe mixture is extracted three times with ethyl acetate
  5. washThe combined ethyl acetate extracts are washed with brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-5551756be5d74d6fb7683a74f6cc72d2
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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