Dichloromethane → HCID 86695065, compound

HRID 574329Notes

Reaction equation

HRID 574329 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:31]=[C:18]3[N:19]=[C:20]([CH3:30])[C:21]([CH:24]([OH:29])[C:25]([O:27][CH3:28])=[O:26])=[C:22]([Cl:23])[N:17]3[N:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:31]=[C:18]3[N:19]=[C:20]([CH3:30])[C:21]([CH:24]([O:29][C:2]([CH3:7])([CH3:3])[CH3:1])[C:25]([O:27][CH3:28])=[O:26])=[C:22]([Cl:23])[N:17]3[N:16]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24247Perchloric AcidHCID 86695064HCID 86695064, compound

Product 1

HCID 86695065HCID 86695065, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

To a suspension of methyl 2-(2-(3-(benzyloxy)phenyl)-7-chloro-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate. (80 mg, 0.18 mmol) in tert-butyl acetate (5 mL) at room temperature was added CH2Cl2 (10 mL) followed by perchloric acid (27 mg, 0.26 mmol). The reaction mixture was stirred for 2 h at room temperature. The reaction mixture was 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 (80 mg, 92%). Used as is in the next step.

Workup

  1. customThe reaction mixture was 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-fadaf57ad880436aab034a0a3ca7ca31
Source dataset
uspto-grants-2015_05
Patent number
US09034882B2

Reaction notes

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