StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Morpholine → N2-[(1S)-1-(5-Fluoropyrimidin-2-yl)ethyl]-N4-(5-methyl-1H-pyrazol-3-yl)-6-(morpholin-4-ylcarbonyl)-5-nitropyrimidine-2,4-diamine

HRID 450389
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 450389
[F:1][C:2]1[CH:3]=[N:4][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([C:17](O)=[O:18])[C:14]([N+:20]([O-:22])=[O:21])=[C:13]([NH:23][C:24]3[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=3)[N:12]=2)[CH3:9])=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:63]1[CH2:68][CH2:67][O:66][CH2:65][CH2:64]1>CN(C=O)C.O.CCOC(C)=O>[F:1][C:2]1[CH:7]=[N:6][C:5]([C@@H:8]([NH:10][C:11]2[N:12]=[C:13]([NH:23][C:24]3[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=3)[C:14]([N+:20]([O-:22])=[O:21])=[C:15]([C:17]([N:63]3[CH2:68][CH2:67][O:66][CH2:65][CH2:64]3)=[O:18])[N:16]=2)[CH3:9])=[N:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 687821322-{[(1S)-1-(5-Fluoropyrimidin-2-yl)ethyl]amino}-6-[(5-methyl-1H-pyrazol-3-yl)amino]-5-nitropyrimidine-4-carboxylic acid2×

Produkt 1

HCID 68780089
N2-[(1S)-1-(5-Fluoropyrimidin-2-yl)ethyl]-N4-(5-methyl-1H-pyrazol-3-yl)-6-(morpholin-4-ylcarbonyl)-5-nitropyrimidine-2,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-{[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]amino}-6-[(5-methyl-1H-pyrazol-3-yl)amino]-5-nitropyrimidine-4-carboxylic acid (Intermediate 50, 406 mg, ˜1 mmol), in DMF (5 ml) were added DIPEA (˜0.3 ml), HATU (456 mg) and morpholine (0.130 ml) at ambient temperature. The resulting mixture was stirred overnight. The mixture was diluted with H2O and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, saturated NaHCO3 (aq) solution, dried and evaporation of the volatiles under reduced pressure gave a colored residue. Purification by column chromatography (ISCO, 50%→70% EtOAc/hexanes) gave the title compound. LCMS: 473 [M+1].

Aufarbeitung

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe combined organic layers were washed with brine, saturated NaHCO3 (aq) solution
  3. customdried
  4. customevaporation of the volatiles under reduced pressure
  5. customgave a colored residue
  6. customPurification by column chromatography (ISCO, 50%→70% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fd56a3750acf4dab85bddc9c2d98fc05
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08486966B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion