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

HRID 472812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472812
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 86670264Methyl 2-(tert-butoxy)-2-(7-chloro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-6-yl)acetateAusbeute 121,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10908tert-Butyl acetateLösungsmittel

Versuchsvorschrift

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) δ ppm 1.27 (9H, s), 2.66 (3H, s), 3.73 (3H, s), 5.66 (1H, s), 6.93 (1H, s), 7.34-7.52 (3H, m), 8.01 (2H, d, J=7.3 Hz).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-84b3c0dbeb9e4e4291bcc78991124fb6
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633200B2

Notizen zur Reaktion

Wird geladen…