Potassium Carbonate → phenyl 3-tert-butyl-1-methyl-1H-pyrazol-5-ylcarbamate

HRID 871507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871507
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([CH3:11])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>C1COCC1>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:19](=[O:20])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]([CH3:11])[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 27352873-tert-Butyl-1-methyl-1H-pyrazol-5-amine

Produkt 1

HCID 46196890phenyl 3-tert-butyl-1-methyl-1H-pyrazol-5-ylcarbamateAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

According to the procedure described in Example 161C, 3-tert-butyl-1-methyl-1H-pyrazol-5-amine (1.0 g, 6.5 mmol), and K2CO3 (1.17 g, 8.5 mmol) in THF (15 mL) were reacted with phenyl chloroformate (1.12 g, 7.2 mmol). The crude product was purified by silica gel chromatography with 0-50% EtOAc/hexane gradient to afford phenyl 3-tert-butyl-1-methyl-1H-pyrazol-5-ylcarbamate as solid (0.53 g, 31%). 1H NMR (300 MHz, DMSO-d6) δ 10.2 (s, 1H), 7.43 (m, 2H), 7.25 (m, 3H), 6.06 (s, 1H), 3.66 (s, 3H), 1.25 (s, 9H); LC-MS (ESI) m/z 274 (M+H)+.

Aufarbeitung

  1. customThe crude product was purified by silica gel chromatography with 0-50% EtOAc/hexane gradient

Quellen und Nachweise

ORD-Eintrag
ord-c7be22070d8545438e607815cdf979f9
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969587B2

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