HCID 60886989, compound → 1-(4-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol

HRID 577716Notes

Reaction equation

HRID 577716 reaction equation
[CH3:1][C:2]([OH:13])([CH3:12])[CH2:3][N:4]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[N:5]1.[H][H]>CO.[Pd]>[NH2:9][C:7]1[CH:6]=[N:5][N:4]([CH2:3][C:2]([CH3:12])([OH:13])[CH3:1])[CH:8]=1

Participants

5

Reactant 2

HCID 60886989HCID 60886989, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 671121581-(4-amino-1H-pyrazol-1-yl)-2-methylpropan-2-olYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

2-methyl-1-(4-nitro-1H-pyrazol-1-yl)propan-2-ol (2.0 g, 10.8 mmol) was dissolved in MeOH (50 mL) and 10% Pd/C (240 mg) was added. A hydrogen balloon was fitted over the reaction and the reaction was allowed to stir at rt for 16 hrs. The reaction was checked using the polar APCI method and LCMS showed 70% complete with 30% starting material remaining. Another 200 mg of 10% Pd/C was added and the balloon was re-charged with fresh hydrogen. After 4 hrs, the reaction was complete. The reaction was filtered through Celite, washing with MeOH (three×50 mL) and the combined filtrate was concentrated to dryness. Purification was accomplished via flash chromatography eluting with gradient of 3%-20% MeOH in DCM. The pure fractions were pooled and concentrated to afford the title compound (1.4 g, 84% yield) as a purple solid. 1H NMR (400 MHz, chloroform-d) δ ppm 1.14 (s, 6H), 3.92 (s, 2H), 7.04 (s, 1H), 7.19 (s, 1H); m/z (APCI+) for C7H13N3O 156.0 (M+H)+.

Workup

  1. waitAfter 4 hrs
  2. filtrationThe reaction was filtered through Celite
  3. washwashing with MeOH (three×50 mL)
  4. concentrationthe combined filtrate was concentrated to dryness
  5. customPurification
  6. washeluting with gradient of 3%-20% MeOH in DCM
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-db24d13a177a4abcbedbfd1c280e1263
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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