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

HRID 645513
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 645513
C([O:4][C:5]([C:7]1[C:8]([O:15][CH2:16][CH:17]2[CH2:24][CH2:23][C:20]3([CH2:22][CH2:21]3)[CH2:19][CH2:18]2)=[N:9][C:10]([C:13]#[N:14])=[N:11][CH:12]=1)=[O:6])C=C.N1CCOCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]([C:10]1[N:9]=[C:8]([O:15][CH2:16][CH:17]2[CH2:24][CH2:23][C:20]3([CH2:22][CH2:21]3)[CH2:19][CH2:18]2)[C:7]([C:5]([OH:6])=[O:4])=[CH:12][N:11]=1)#[N:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 8083MorpholineHCID 687066042-Cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester

Produkt 1

HCID 687069622-Cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of a 2-cyano-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid allyl ester (0.096 mmol) in THF (1.0 mL) are added Pd(PPh3)4 (tetrakis(triphenylphosphine)palladium) (0.0096 mmol) and morpholine (0.19 mmol) at room temperature. The reaction mixture is stirred at room temperature for 0.5 h and the reaction is quenched by the addition of sat. aq. NaHCO3. The mixture is extracted with ether. The aqueous layer is acidified to pH 2 with sat. aq. KHSO4. The mixture is extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude titled compound.

Aufarbeitung

  1. customthe reaction is quenched by the addition of sat. aq. NaHCO3
  2. extractionThe mixture is extracted with ether
  3. extractionThe mixture is extracted with AcOEt
  4. washThe organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1360f99a564e4119b2fce54cea85024d
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07704996B2

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