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Dimethylformamide → [4-N-(Piperonyloxycarbonyl)-cytosin-1-yl]-acetic acid ethyl ester

HRID 1064611
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1064611
[N:1]1([CH2:9][C:10]([OH:12])=[O:11])[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].C(N1C=CN=C1)(N1[CH:19]=[CH:18]N=C1)=O.[CH2:25]([OH:35])[C:26]1[CH:34]=[CH:33][C:32]2[O:31][CH2:30][O:29][C:28]=2[CH:27]=1.CN([CH:39]=[O:40])C>>[CH2:18]([O:11][C:10](=[O:12])[CH2:9][N:1]1[CH:8]=[CH:7][C:5]([NH:6][C:39]([O:35][CH2:25][C:26]2[CH:34]=[CH:33][C:32]3[O:31][CH2:30][O:29][C:28]=3[CH:27]=2)=[O:40])=[N:4][C:2]1=[O:3])[CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 10322Piperonyl alcoholHCID 682631,1'-CarbonyldiimidazoleHCID 21868458(4-Amino-2-oxo-2H-pyrimidin-1-yl)-acetic acid

Produkt 1

HCID 68524231[4-N-(Piperonyloxycarbonyl)-cytosin-1-yl]-acetic acid ethyl esterAusbeute 96 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The reaction mixture of (cytosin-1-yl)-acetic acid (3.94 g, 20 mmol) and 1,1′-carbonyldiimidazole (4.86 g, 30 mmol) in DMF was stirred for 25 min. at 100° C. Then, piperonyl alcohol (6.08 g, 40 mmol) was added to the reaction mixture. The resulting reaction mixture was allowed to cool to room temperature for 2 h. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (100 mL). The solution was washed with water (100 mL×2), dried over MgSO4, and filtered. The filtrate was concentrated in vacuo and treated with ethyl ether to afford white solid. The solid was filtered off and dried in vacuo to give the desired product (7.20 g, 96%). 1H-NMR (500 MHz; DMSO-d6) δ 10.77 (s, 1H), 8.04 (d, 1H), 7.04 (d, 1H), 7.00 (s, 1H), 6.92 (s, 2H), 6.02 (s, 2H), 5.09 (s, 2H), 4.61 (s, 2H), 4.15 (q, 2H), 1.19 (t, 3H).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperatureto cool to room temperature for 2 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  5. washThe solution was washed with water (100 mL×2)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. additiontreated with ethyl ether
  10. customto afford white solid
  11. filtrationThe solid was filtered off
  12. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-958182d48e514af89223823579fb856b
Quelldatensatz
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06969766B2

Notizen zur Reaktion

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