Sodium Hydroxide → 6-Amino-1,3-dibutyluracil

HRID 965186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 965186
[C:1]([CH2:3][C:4]([N:6]([CH2:14][CH2:15][CH2:16][CH3:17])[C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])=[O:5])#[N:2].[OH-].[Na+]>CO>[CH2:10]([N:9]1[C:1]([NH2:2])=[CH:3][C:4](=[O:5])[N:6]([CH2:14][CH2:15][CH2:16][CH3:17])[C:7]1=[O:8])[CH2:11][CH2:12][CH3:13]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 10376972N-(2-cyanoacetyl)-N,N'-dibutylurea

Produkt 1

HCID 99918436-Amino-1,3-dibutyluracilAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

N,N-Di-n-butylurea (34.45 g, 0.2 mmol), cyanoacetic acid (19.56 g, 0.23 mol), and acetic anhydride (81.66 ml, 0.8 mol) were heated at 80° C. for 2 h under nitrogen and solvent was removed by rotary evaporation to yield N-(2-cyanoacetyl)-N,N'-dibutylurea. The N-(2-cyanoacetyl)-N,N'-dibutylurea was dissolved in methanol (100 ml) and 4N NaOH (100 ml) was added. The reaction mixture was cooled for 30 min with stirring and the solid was filtered and dried to yield 1,3-di-n-butyl-6-aminouracil (47.04 g, 99.5%) as a colorless solid, m.p. 90.1°-92.4° C.; 1H NMR (DMSO-d6) δ1.72-1.93 (m, 6H, 2×CH3, 1.18-1.33 (m, 4H, 2×CH2), 1.39-1.52 (M, 4H, 2×CH2), 3.70 (t, 2H, N--CH2), 3.76 (t, 2H, N--CH2), 4.64 (s, 1H, H-4), 6.77 (br s, exchangeable with D2O, 2H, NH2).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled for 30 min
  2. filtrationthe solid was filtered
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1e5b46dee08a4ed3abc1d30f4e634eca
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05773423

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