Dimethylamine → 9-{2-[1-(4-Dimethylaminomethylbenzyl)piperidin-4-yl]ethyl}-8-methoxy-2-(2-methoxyethoxy)-9H-purin-6-ylamine

HRID 1666205Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666205
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:33][CH3:34])[N:6]2[CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][C:25]2[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)[CH2:20][CH2:19]1.[CH3:35][NH:36][CH3:37].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1COCC1>[CH3:35][N:36]([CH2:29][C:28]1[CH:31]=[CH:32][C:25]([CH2:24][N:21]2[CH2:20][CH2:19][CH:18]([CH2:17][CH2:16][N:6]3[C:5]([O:33][CH3:34])=[N:4][C:3]4[C:7]3=[N:8][C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[N:10][C:2]=4[NH2:1])[CH2:23][CH2:22]2)=[CH:26][CH:27]=1)[CH3:37]

Komponenten

6

Edukt 4

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 592880284-(4-{2-[6-Amino-8-methoxy-2-(2-methoxyethoxy)purin-9-yl]ethyl}-piperidin-1-ylmethyl)benzaldehyde

Produkt 1

HCID 592880309-{2-[1-(4-Dimethylaminomethylbenzyl)piperidin-4-yl]ethyl}-8-methoxy-2-(2-methoxyethoxy)-9H-purin-6-ylamineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The compound (0.31 g, 1.66 mmol) obtained in Step (ii) was dissolved in THF (10 ml), and thereto were added at 0° C. dimethylamine (2M THF solution, 2.62 ml, 5.24 mmol) and sodium triacetoxy borohydride (0.56 g, 2.62 mmol), and the mixture was stirred at room temperature for 20 hours. The mixture was cooled to 0° C., and thereto was added a saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted three times with chloroform/ethanol=3/1. The extract was dried over magnesium sulfate, concentrated, and purified by silica gel column (chloroform/methanol/28% aqueous ammonia=100/5/0 to 100/5/1) to give the title compound (0.28 g, 0.57 mmol) as a white solid. Yield: 87%.

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionthe mixture was extracted three times with chloroform/ethanol=3/1
  3. dry with materialThe extract was dried over magnesium sulfate
  4. concentrationconcentrated
  5. custompurified by silica gel column (chloroform/methanol/28% aqueous ammonia=100/5/0 to 100/5/1)

Quellen und Nachweise

ORD-Eintrag
ord-3748827f543049938de508b09c604030
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044056B2

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