Cesium carbonate → HCID 11681659, Verbindung

HRID 929405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929405
[NH2:1][C:2]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.C([O-])([O-])=O.[Cs+].[Cs+].[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([O-:24])=[O:23]>CN(C=O)C.[Cl-].[Na+].O>[CH2:12]([NH:11][C:9]1[N:8]=[C:7]2[C:3]([N:4]=[CH:5][N:6]2[CH2:29][C:28]2[CH:31]=[CH:32][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)=[C:2]([NH2:1])[N:10]=1)[CH2:13][CH2:14][CH3:15]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 660114-Nitrobenzyl bromideHCID 178448875HCID 178448875, Verbindung

Produkt 1

HCID 11681659HCID 11681659, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

6-amino-2-butylamino-9H-purine, intermediate 1 (9.93 g, 48.2 mmol) and Cs2CO3 (15.69 g, 48.2 mmol) were suspended in DMF (200 mL). 4-nitrobenzyl bromide (12.48 mg, 57.8 mmol) was added thereto and the mixture was stirred at rt for 18 h. After condensing the suspension in vacuo, to the residue was added brine and the mixture was extracted with ethyl acetate. The organic layer was washed the mixture was with brine, dried on MgSO4, filtered and the solvent was evaporated in vacuo. The residue was purified on column of silica gel (5% MeOH/DCM) to give the subject compound (11.51 g, yield 70%). Intermediate 59 was characterized by the following spectroscopic data: 1H NMR (DMSO-d6, 300 MHz) δ (ppm) 8.19 (d, 2H), 7.83 (s, 1H), 7.49 (d, 2H), 6.69 (sl, 2H), 6.25 (t, 1H), 5.34 (s, 2H), 3.17 (m, 2H), 1.41 (m, 2H), 1.25 (q, 2H), 0.83 (t, 3H).

Aufarbeitung

  1. customAfter condensing the suspension in vacuo
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed the mixture
  4. customdried on MgSO4
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified on column of silica gel (5% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-808857ecbb31404e9ed15f6a984b1dd7
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09295732B2

Notizen zur Reaktion

Wird geladen…