N,N-Dimethylaniline → HCID 86667835, compound

HRID 1913216Notes

Reaction equation

HRID 1913216 reaction equation
O[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH2:11][CH:12]2[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH:3]=1.CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:34]>>[Cl:34][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH2:11][CH:12]2[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]2)[CH:3]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178468818HCID 178468818, compound

Product 1

HCID 86667835HCID 86667835, compound

Procedure

To a 100 mL round-bottom flask was charged ethyl 4-((7-hydroxypyrazolo[1,5-a]pyrimidin-5-yl)methyl)cyclohexanecarboxylate (Int-4f, 2.48 g, 8.19 mmol), N,N-dimethylaniline (4 mL) and POCl3 (40 mL). The resulting solution was allowed to stir at room temperature for 18 hours. After 18 hours, the solvent was removed in vacuo. The residue was cooled to 0° C. in ice bath. The cooled residue was slowly quenched with saturated NaHCO3 (aq), and then extracted with DCM (x3). The combined organic extracts were dried over Na2SO4 and the residue purified via silica gel chromatography to yield the title compound as clear oil. Yield=2.29 g.

Workup

  1. waitAfter 18 hours
  2. customthe solvent was removed in vacuo
  3. temperatureThe residue was cooled to 0° C. in ice bath
  4. customThe cooled residue was slowly quenched with saturated NaHCO3 (aq)
  5. extractionextracted with DCM (x3)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. customthe residue purified via silica gel chromatography

Sources & evidence

ORD record
ord-f185b279622c4c1eba15cb561f0e3f84
Source dataset
uspto-grants-2013_12
Patent number
US08609675B2

Reaction notes

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