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

HRID 271260

反応式

HRID 271260 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d26ba319f471470d8cfa8588437719c1
出典データセット
uspto-grants-2008_11
特許番号
US07452894B2

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