N,N-Dimethylaniline → HCID 86664785, compound

HRID 2047119Notes

Reaction equation

HRID 2047119 reaction equation
O[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)[CH:3]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:34])=O>>[Cl:34][C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)[CH:3]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178451768HCID 178451768, compound

Product 1

HCID 86664785HCID 86664785, compound

Conditions

Temperature
50 °C

Procedure

To a mixture of tert-butyl 3-(7-hydroxypyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidine-1-carboxylate (3.70 g, 12.0 mmol) and dimethylaniline (4.0 mL, 30 mml) was added phosphoryl trichloride (40 mL). The mixture was heated at 50° C. for 5 h and concentrated in vacuo. The residue was diluted with methylene chloride (100 mL) and quenched with saturated NaHCO3 (100 mL). The mixture was separated and the aqueous layer was extracted with chloride (100 mL×2). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by Biotage (CH2Cl2/EtOAc, 20:1 to 4:1). LC/MS RT=2.09 min (5 min method). Mass calculated for, M+H 322.12, observed 337.14.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with methylene chloride (100 mL)
  3. customquenched with saturated NaHCO3 (100 mL)
  4. customThe mixture was separated
  5. extractionthe aqueous layer was extracted with chloride (100 mL×2)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by Biotage (CH2Cl2/EtOAc, 20:1 to 4:1)
  10. customLC/MS RT=2.09 min (5 min method)

Sources & evidence

ORD record
ord-54dc07e3957047a48c7a43c88b45921e
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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