Dichloromethane → Methyl 2-tert-butoxy-2-(3,7-dichloro-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

HRID 472848Notes

Reaction equation

HRID 472848 reaction equation
[Cl:1][C:2]1[C:3]([CH3:19])=[N:4][N:5]2[C:10]([Cl:11])=[C:9]([CH:12]([OH:17])[C:13]([O:15][CH3:16])=[O:14])[C:8]([CH3:18])=[N:7][C:6]=12.C(Cl)Cl.Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C.C(OCC)(=O)C>[C:9]([O:17][CH:12]([C:9]1[C:8]([CH3:18])=[N:7][C:6]2[N:5]([N:4]=[C:3]([CH3:19])[C:2]=2[Cl:1])[C:10]=1[Cl:11])[C:13]([O:15][CH3:16])=[O:14])([CH3:12])([CH3:10])[CH3:8]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 24247Perchloric AcidHCID 86670282Methyl 2-(3,7-dichloro-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate

Product 1

HCID 86670283Methyl 2-tert-butoxy-2-(3,7-dichloro-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)acetateYield 181.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10908tert-Butyl acetateSolvent

Procedure

To a suspension of methyl 2-(3,7-dichloro-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate (80 mg, 0.26 mmol) in tert-butyl acetate (1.5 mL) at room temperature was added CH2Cl2 (1.5 mL) followed by perchloric acid (40 mg, 2.1 mmol). The reaction mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with ethyl acetate (15 mL). The organic phase was washed with saturated NaHCO3 (2×10 mL), followed by water (1×10 mL) and dried over sodium sulfate. The solvent was evaporated. Purification by silica gel chromatography provided the title compound (85 mg, 90%). Used as is in the next step.

Workup

  1. washThe organic phase was washed with saturated NaHCO3 (2×10 mL)
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated
  4. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-8ef0189e279e4c98b063051719800651
Source dataset
uspto-grants-2014_01
Patent number
US08633200B2

Reaction notes

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