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

HRID 631464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 631464
[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, to a suspension of 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) was added phenyl chloroformate (1.12 g, 7.2 mmol). The crude product was purified by silica gel chromatography with 0-50% EtOAc/hexane as eluants 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 as eluants

Quellen und Nachweise

ORD-Eintrag
ord-8eb8acc708c8409397f3f4768be09925
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09320739B2

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