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Water → 2-Cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester

HRID 645512
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 645512
[CH2:1]([O:4][C:5]([C:7]1[C:8]([O:14][CH2:15][CH:16]2[CH2:23][CH2:22][C:19]3([CH2:21][CH2:20]3)[CH2:18][CH2:17]2)=[N:9][C:10](Cl)=[N:11][CH:12]=1)=[O:6])[CH:2]=[CH2:3].[C-]#N.[K+].C1N2CC[N:29](CC2)[CH2:28]1.O>CS(C)=O>[CH2:1]([O:4][C:5]([C:7]1[C:8]([O:14][CH2:15][CH:16]2[CH2:23][CH2:22][C:19]3([CH2:21][CH2:20]3)[CH2:18][CH2:17]2)=[N:9][C:10]([C:28]#[N:29])=[N:11][CH:12]=1)=[O:6])[CH:2]=[CH2:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 9032Potassium CyanideHCID 9237DabcoHCID 866277972-Chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester

Produkt 1

HCID 687066042-Cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Versuchsvorschrift

To a solution of the 2-chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester (0.62 mmol) in DMSO (1.0 mL) are added KCN (0.94 mmol), DABCO (0.19 mmol), and H2O (0.10 mL) at room temperature. The reaction mixture is stirred at room temperature for 0.5 h and the reaction is quenched by the addition of water. The mixture is extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue is purified by silica gel column chromatography to give the titled compound; 1H NMR (CDCl3) δ 0.19-0.20 (m, 2H), 0.21-0.33 (m, 2H), 0.91-0.96 (m, 2H), 1.23-1.33 (m, 3H), 1.72-1.85 (m, 4H), 4.38 (d, 2H), 4.84 (d, 2H), 5.31-5.45 (m, 1H), 9.01 (s, 1H).

Aufarbeitung

  1. customthe reaction is quenched by the addition of water
  2. extractionThe mixture is extracted with AcOEt
  3. washThe organic extracts are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue is purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-73f78fb6c2eb48488661676f59f103ca
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07704996B2

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