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

HRID 271260

Reaction equation

HRID 271260 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 598350989-(2-Cyclohexylethyl)-6-(2-furyl)-9H-purine-2-amineYield 58.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d26ba319f471470d8cfa8588437719c1
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Linked notes

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