Dichloromethane → Methyl 2-(tert-butoxy)-2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

HRID 574324Notes

Reaction equation

HRID 574324 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:10]=[C:6]2[N:5]=[C:4]([CH3:17])[C:3]=1[CH:18]([OH:23])[C:19]([O:21][CH3:22])=[O:20].C(Cl)Cl.Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C>[C:3]([O:23][CH:18]([C:3]1[C:4]([CH3:17])=[N:5][C:6]2[N:7]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:10]=2)[C:2]=1[Cl:1])[C:19]([O:21][CH3:22])=[O:20])([CH3:18])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24247Perchloric AcidHCID 86670265Methyl 2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate

Product 1

HCID 86670264Methyl 2-(tert-butoxy)-2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetateYield 121.6%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

To a suspension of methyl 2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)-2-hydroxyacetate (100 mg, 0.301 mmol) in tert-butyl acetate (2 mL) at room temperature was added CH2Cl2 (2 mL) followed by perchloric acid (0.027 mL, 0.452 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 (71 mg, 60.7%). 1H-NMR (500 MHz, CDCl3) δ1.27 (9 H, s), 2.66 (3 H, s), 3.73 (3 H, s), 5.66 (1 H, s), 6.93 (1 H, s), 7.34-7.52 (3 H, m), 8.01 (2 H, d, J=7.3 Hz).

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-75d549fafd7947a6abcfc2a40a81ab2e
Source dataset
uspto-grants-2015_05
Patent number
US09034882B2

Reaction notes

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