Perchloric Acid → HCID 66692364, compound

HRID 472823Notes

Reaction equation

HRID 472823 reaction equation
[OH:1][CH:2]([C:7]1[C:8]([CH3:23])=[N:9][C:10]2[N:11]([N:20]=[CH:21][CH:22]=2)[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)[C:3]([O:5][CH3:6])=[O:4].Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C>[C:7]([O:1][CH:2]([C:7]1[C:8]([CH3:23])=[N:9][C:10]2[N:11]([N:20]=[CH:21][CH:22]=2)[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)[C:3]([O:5][CH3:6])=[O:4])([CH3:8])([CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 66692083HCID 66692083, compound

Product 1

HCID 66692364HCID 66692364, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

To a suspension of methyl 2-hydroxy-2-(5-methyl-7-p-tolylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (40 mg, 0.128 mmol) in tert-butyl acetate (1 mL) at room temperature was added perchloric acid (0.015 mL, 0.257 mmol). The reaction mixture was stirred for 2 h at room temperature before being quenched with water and diluted with ethyl acetate. The organic phase was washed with saturated NaHCO3 and dried over sodium sulfate. The solvent was evaporated. Purification by silica gel chromatography provided the title compound (26 mg, 55.1%). 1H-NMR (500 MHz, CDCl3) δ ppm 0.96 (9H, m), 2.46 (3H, s), 2.66 (3H, s), 3.78 (3H, s), 5.10 (1H, s), 6.59 (1H, d, J=2.4 Hz), 7.37-7.40 (2H, m), 7.43-7.55 (2H, m), 7.99 (1H, d, J=2.4 Hz).

Workup

  1. custombefore being quenched with water
  2. additiondiluted with ethyl acetate
  3. washThe organic phase was washed with saturated NaHCO3
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-77f3f9a71268449c8d99807f276e4027
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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