Sodium Hydroxide → 5-(3-ethoxy-2-thienyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

HRID 1421482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1421482
[CH2:1]([O:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]([NH:11][C:12]1[C:13]([CH2:21][CH2:22][CH3:23])=[N:14][N:15]([CH3:20])[C:16]=1[C:17]([NH2:19])=[O:18])=O)[CH3:2].[OH-].[Na+]>C(O)C.O>[CH2:1]([O:3][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]1[NH:19][C:17](=[O:18])[C:16]2[N:15]([CH3:20])[N:14]=[C:13]([CH2:21][CH2:22][CH3:23])[C:12]=2[N:11]=1)[CH3:2]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 53256814-(3-Ethoxythiophene-2-carboxamido)-1-methyl-3-n-propylpyrazole-5-carboxamide

Produkt 1

HCID 1354942865-(3-ethoxy-2-thienyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-oneAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3 (1.15 g, 3.42 mmol), NaOH (284 mg, 7.1 mmol) in ethanol (11 mL) and water (34 mL) was heated at 80° C. for 65 h. After cooling to r.t. a white precipitate was formed. Filtration and drying under vacuum gave 0.625 g of the product. The filtrate was extracted with CH2Cl2, and the organic phase was washed with 1N HCl and brine, dried with MgSO4. Evaporation of the solvent gave additional product; mp: 151-152° C.; 1H NMR (CDCl3) δ 1.00 (t, J=7 Hz, 3 H), 1.54 (t, J=7 Hz, 3 H), 1.82 (sxt, J=7 Hz, 2 H), 2.86 (t, J=7 Hz, 2 H), 4.23 (s, 3 H), 4.34 (q, J=7 Hz, 2 H), 6.87 (d, J=6 Hz, 1 H), 7.37 (d, J=6 Hz, 1 H); MS (m/z): 319 (MH+).

Aufarbeitung

  1. temperatureAfter cooling to r.t. a white precipitate
  2. customwas formed
  3. filtrationFiltration
  4. customdrying under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-0d559818b3d1417ca84109d75643c4cb
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06077841

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