Potassium Hydroxide → Tert-butyl 5-amino-3-[(3,5-dimethoxyphenyl)methoxy]pyrazole-1-carboxylate

HRID 16751

Reaktionsgleichung

Reaktionsgleichung von HRID 16751
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][O:14][C:15]2[CH:16]=[C:17]([NH2:20])[NH:18][N:19]=2)[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1.C(=O)(OC(C)(C)C)[O:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=O>O.ClCCl>[NH2:20][C:17]1[N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:22])[N:19]=[C:15]([O:14][CH2:13][C:7]2[CH:6]=[C:5]([O:4][CH3:3])[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=2)[CH:16]=1

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 574403815-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine

Produkt 1

HCID 66589741Tert-butyl 5-amino-3-[(3,5-dimethoxyphenyl)methoxy]pyrazole-1-carboxylateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Potassium hydroxide (11.19 g, 199.4 mmol) dissolved in water (44.8 ml) was added to a solution of 5-[(3,5-dimethoxyphenyl)methoxy]-2H-pyrazol-3-amine (7.121 g) dissolved in dichloromethane (40 ml). (2-Methylpropan-2-yl)oxycarbonyl tert-butyl carbonate (6.8 g, 31.2 mmol) dissolved in DCM (35 ml) was added and the reaction mixture was stirred vigorously at room temperature for 4 h. The reaction mixture was separated and the organic layer was washed with water (2×15 ml), brine (2×15 ml), dried over sodium sulphate, filtered, evaporated and dried in vacuo to give tert-butyl 5-amino-3-[(3,5-dimethoxyphenyl)methoxy]pyrazole-1-carboxylate (8.70 g, 99%) as a cream solid.

Aufarbeitung

  1. additionwas added
  2. customThe reaction mixture was separated
  3. washthe organic layer was washed with water (2×15 ml), brine (2×15 ml)
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4cf83e5733c04d5ea4181ad37e77c6c7
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737149B2

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