5-(5-Bromo-4-oxo-pentyl)-thiophene-2-carboxylic acid methyl ester → 5-[3-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)-propyl]-thiophene-2-carboxylic acid methyl ester

HRID 889074

Reaktionsgleichung

Reaktionsgleichung von HRID 889074
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[CH:5]=[C:4]([NH2:9])[N:3]=1.[CH3:10][O:11][C:12]([C:14]1[S:15][C:16]([CH2:19][CH2:20][CH2:21][C:22](=O)[CH2:23]Br)=[CH:17][CH:18]=1)=[O:13]>CN(C=O)C>[CH3:10][O:11][C:12]([C:14]1[S:15][C:16]([CH2:19][CH2:20][CH2:21][C:22]2[NH:9][C:4]3[N:3]=[C:2]([NH2:1])[NH:7][C:6](=[O:8])[C:5]=3[CH:23]=2)=[CH:17][CH:18]=1)=[O:13]

Komponenten

4

Edukt 2

HCID 592688525-(5-Bromo-4-oxo-pentyl)-thiophene-2-carboxylic acid methyl esterHCID 1354087632-Aminoisocytosine

Produkt 1

HCID 1363814275-[3-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)-propyl]-thiophene-2-carboxylic acid methyl esterAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 2,6-diaminopyrimidin-4-one (315 mg, 2.5 mmol) in anhydrous DMF (15 mL) was added 7 (about 2.4 mmol). The resulting mixture was stirred under N2 at room temperature for 3 days. After evaporation of solvent under reduced pressure, MeOH (20 mL) was added followed by silica gel (1.5 g). The resulting plug was loaded on to a silica gel column (3.5×12 cm) and eluted with CHCl3 followed by 3% MeOH in CHCl3 and then 5% MeOH in CHCl3. Fractions with an Rf=0.56 (MeOH/CHCl3 1:5) were pooled and evaporated to afford 300 mg of 8 as white powder in 38% yield. 1H NMR (DMSO-d6): δ 1.89-1.97 (m, 2H), 2.49-2.54 (t, J=7.2 Hz, 2H), 2.82-2.85 (t, J=7.2 Hz, 2H), 3.78 (s, 3H), 5.89 (s, 1H), 5.96 (s, 2H), 6.97-6.98 (d, J=3.6 Hz, 1H), 7.64-7.65 (d, J=3.6 Hz, 1H), 10.13 (s, 1H), 10.82 (s, 1H).

Aufarbeitung

  1. customAfter evaporation of solvent under reduced pressure, MeOH (20 mL)
  2. additionwas added
  3. washeluted with CHCl3
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-bd002359ffcb4b21bf736a202cd2eecd
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252804B2

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