Potassium Carbonate → 3-[5-(6-Chloropurin-9-yl)pentyloxy]benzamide

HRID 1292140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1292140
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=[O:12].[Cl:17][C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[NH:20][CH:21]=[N:22]2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:17][C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH2:13])=[O:12]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 53592776-ChloropurineHCID 183546093-(Bromopentyloxy)benzamide

Produkt 1

HCID 183546243-[5-(6-Chloropurin-9-yl)pentyloxy]benzamideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-(bromopentyloxy)benzamide (500 mg, 1.7 mmols), 6-chloropurine (270 mg, 1.7 mmols) and potassium carbonate (240 mg, 1.7 mmols) in DMF (7.5 ml) was stirred for two days at room temperature. The solvent was then removed under vacuum (0.001 mmHg) and the white solid (mixture of N7 and N9 isomers) was chromatographed (silica, 10% MeOH/CH2CI2) to give a single product (N9 isomer) as a glass. This was triturated with ether (=5 ml) to give a white solid which was recrystallised from ethyl acetate to give the product (120 mg, 0.33 mmols, 20% yield)

Aufarbeitung

  1. customThe solvent was then removed under vacuum (0.001 mmHg)
  2. additionthe white solid (mixture of N7 and N9 isomers)
  3. customwas chromatographed (silica, 10% MeOH/CH2CI2)
  4. customto give a single product (N9 isomer) as a glass
  5. customThis was triturated with ether (=5 ml)
  6. customto give a white solid which
  7. customwas recrystallised from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c72acf8eb11c4393a822f858faf15e12
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05756510

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