1-Butanol → HCID 178448875, Verbindung

HRID 2197475Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2197475
Cl[C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH2:11])[N:3]=1.[CH2:12]([NH2:16])[CH2:13][CH2:14][CH3:15].C(O)CCC>CS(C)=O>[CH2:12]([NH:16][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH2:11])[N:3]=1)[CH2:13][CH2:14][CH3:15]

Komponenten

5

Edukt 3

HCID 2631-ButanolHCID 8007ButylamineHCID 949042-Chloroadenine

Produkt 1

HCID 178448875HCID 178448875, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

2-chloroadenine (1) (1.60 g, 9.44 mmol) was divided among three microwave vials (10-20 mL), each containing Butylamine (4 mL), 1-Butanol (10 mL,), and DMSO (1 mL). Each vial was heated to 170° C. for 90 minutes. After reaction completion the solvent was removed by rotary evaporation and the product was purified on flash column eluting 10% methanol in ethylacetate. Evaporation of solvent gave 1.62 g (83%) of 64 as an off white solid. 1H NMR (300 MHz, DMSO) δ 0.877 (t, 3H), 1.29 (m, 2H), 1.45 (m, 2H), 3.17 (t, 2H), 6.49 (s, 2H), 7.61 (s, 1H), 12.1 (s, 1H). LCMS: m/z for C9H14N6++H observed 207.2 at 1.40 minutes of a 3.5 minute run, gradient 5-95% CH3CN in H2O.

Aufarbeitung

  1. customAfter reaction completion the solvent
  2. customwas removed by rotary evaporation
  3. customthe product was purified on flash column
  4. washeluting 10% methanol in ethylacetate
  5. customEvaporation of solvent

Quellen und Nachweise

ORD-Eintrag
ord-e2b86ccd86d34646be0b9cf1d8fe480b
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338593B2

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