Dimethyl Sulfoxide → N-methyl-4-(2-(4-((4-phenylphthalazin-1-yl)methyl)phenoxy)pyridin-3-yl)pyrimidin-2-amine

HRID 911149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 911149
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH3:15])[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[C:16]1([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=3)=[N:24][N:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>CCOC(C)=O>[CH3:15][NH:14][C:10]1[N:9]=[C:8]([C:7]2[C:2]([O:39][C:36]3[CH:35]=[CH:34][C:33]([CH2:32][C:25]4[C:26]5[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:22]([C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=5)=[N:23][N:24]=4)=[CH:38][CH:37]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:13]=[CH:12][N:11]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 161090044-(2-chloro-3-pyridinyl)-N-methyl-2-pyrimidinamineHCID 577562584-((4-Phenylphthalazin-1-yl)methyl)phenol

Produkt 1

HCID 57756268N-methyl-4-(2-(4-((4-phenylphthalazin-1-yl)methyl)phenoxy)pyridin-3-yl)pyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

To a mixture of 4-(2-chloropyridin-3-yl)-N-methylpyrimidin-2-amine (0.0500 g, 0.23 mmol), 4-((4-phenylphthalazin-1-yl)methyl)phenol (0.071 g, 0.23 mmol) and cesium carbonate (0.15 g, 0.45 mmol) was added DMSO (0.5 mL). The resulting mixture was heated to 130° C. in a sealed tube for 15 hours, then diluted with EtOAc and extracted with saturated sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered and concentrated. The crude concentrate was purified by Gilson reverse-phase HPLC (0.1% TFA in ACN/water; 15-95% ACN; 40 mL/min). Diluted product with DCM and extracted with saturated sodium bicarbonate. Dried organics over sodium sulfate, filtered and concentrated. Lyophilized concentrate to obtained N-methyl-4-(2-(4-((4-phenylphthalazin-1-yl)methyl)phenoxy)pyridin-3-yl)pyrimidin-2-amine as a white solid. MS m/z=497 [M+H]+. Calc'd for C31H24N6O: 496.58.

Aufarbeitung

  1. extractionextracted with saturated sodium bicarbonate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. concentrationThe crude concentrate
  6. customwas purified by Gilson reverse-phase HPLC (0.1% TFA in ACN/water; 15-95% ACN; 40 mL/min)
  7. extractionDiluted product with DCM and extracted with saturated sodium bicarbonate
  8. filtrationDried organics over sodium sulfate, filtered
  9. concentrationconcentrated
  10. concentrationLyophilized concentrate

Quellen und Nachweise

ORD-Eintrag
ord-fad3a8a43b024c92a25a15c8350137f5
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022221B2

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