2-Bromopropane → (3-Chlorobenzyl)-(2-fluoro-9-isopropyl-9H-purin-6-yl)amine

HRID 2047660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047660
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]1[N:15]=[C:14]([F:16])[N:13]=[C:12]2[C:8]=1[N:9]=[CH:10][NH:11]2.C(=O)([O-])[O-].[K+].[K+].Br[CH:27]([CH3:29])[CH3:28].C(Cl)Cl.CCOCC.CO>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][NH:6][C:7]1[N:15]=[C:14]([F:16])[N:13]=[C:12]2[C:8]=1[N:9]=[CH:10][N:11]2[CH:27]([CH3:29])[CH3:28]

Komponenten

6

Edukt 4

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 22565053DCM ether MeOHHCID 178506014HCID 178506014, Verbindung

Produkt 1

HCID 57433115(3-Chlorobenzyl)-(2-fluoro-9-isopropyl-9H-purin-6-yl)amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of (3-chloro-benzyl)-(2-fluoro-9H-purin-6-yl)-amine (0.6 g, 2.16 mmol) in dimethylformamide (10 ml) at room temperature under an argon atmosphere, was added powdered, anhydrous potassium carbonate (1.47 g, 5 eq, 10.8 mmol), followed by 2-bromopropane (2.2 ml, 10 eq, 21.6 mmol). The reaction mixture was stirred at room temperature for 24 h, when DCM:ether:MeOH (55:40:5), indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate (50 ml) and water (50 ml). The aqueous phase was extracted with more ethyl acetate (2×50 ml) and the combined organic phase washed with brine (50 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by silica gel flash column chromatography, eluted with CHCl3 to afford the title compound as a slightly yellow gum; Yield: 0.45 g (65%). δH (250 MHz, CDCl3) 1.57 (6H, d, J 7.5, CH[CH3]2), 4.81-4.63 (3 H, m, NHCH2Ar and CHMe2), 5.98 (1 H, s, br, NH), 7.29-7.19 (3 H, m, ArH), 7.34 (1 H, s, br, ArH), 7.42 (1 H, d, J 7.5, ArH), 7.51 (1 H, s, br, NH); δC (250 MHz, CDCl3) 161.93 (C), 156.37 (C), 156.05 (C), 141.33 (C), 140.42 (C), 137.75 (CH), 134.49 (C), 129.92 (CH), 127.69 (CH), 125.81 (CH), 125.64 (CH), 47.43 (CH), 43.82 (CH2), 22.56 (2×CH3); m/z 320.3 (M+H)

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between ethyl acetate (50 ml) and water (50 ml)
  3. extractionThe aqueous phase was extracted with more ethyl acetate (2×50 ml)
  4. washthe combined organic phase washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel flash column chromatography
  8. washeluted with CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-5ee3dcf2c1654eee99168997a77c1dd9
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592581B2

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