2-Cyclohexylethanol → 9-(2-Cyclohexylethyl)-6-(2-furyl)-9H-purine-2-amine

HRID 271260

Reaktionsgleichung

Reaktionsgleichung von HRID 271260
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:14][C:13]([NH2:15])=[N:12][C:11]2[C:7]=1[N:8]=[CH:9][N:10]=2.[CH:16]1([CH2:22][CH2:23]O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>CN(C=O)C.C1COCC1>[CH:16]1([CH2:22][CH2:23][N:10]2[CH:9]=[N:8][C:7]3[C:11]2=[N:12][C:13]([NH2:15])=[N:14][C:6]=3[C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Komponenten

6

Edukt 3

HCID 205082-CyclohexylethanolHCID 97268Di-tert-butyl azodicarboxylateHCID 1785082476-(furan-2-yl)-9H-purin-2-amine

Produkt 1

HCID 598350989-(2-Cyclohexylethyl)-6-(2-furyl)-9H-purine-2-amineAusbeute 58,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 6-(2-furyl)-1H-purine-2-amine (25 mg, 0.12 mmol) in anhydrous DMF (0.5 mL) and anhydrous THF (2 mL) was treated with triphenylphosphine polystyrene (65 mg, 0.25 mmol) and 2-cyclohexylethanol (35 mg, 0.25 mmol), shaken at room temperature for 10 min, treated with di-tert-butyl azodicarboxylate (0.058 g, 0.25 mmol), shaken at room temperature for 16 h, filtered and concentrated in vacuo. The resulting oil was dissolved in CH2Cl2 (2 mL) and TFA (1 mL), shaken for 2 h and concentrated in vacuo. The resulting oil was dissolved in CH2Cl2 (3 mL), shaken with 1-M aq HCl (1 mL) for 15 min and the organic phase concentrated in vacuo and purified by chromatography (SiO2; EtOAc) to give the title compound (22 mg, 57%) as a yellow solid.

Aufarbeitung

  1. stirringshaken at room temperature for 16 h
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting oil was dissolved in CH2Cl2 (2 mL)
  5. stirringTFA (1 mL), shaken for 2 h
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resulting oil was dissolved in CH2Cl2 (3 mL)
  8. stirringshaken with 1-M aq HCl (1 mL) for 15 min
  9. concentrationthe organic phase concentrated in vacuo
  10. custompurified by chromatography (SiO2; EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-d26ba319f471470d8cfa8588437719c1
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452894B2

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