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1,3-Dibromopropane → 9-[3-(1-Azetidinyl)propyl]-2-(butyloxy)-8-(methyloxy)-9H-purin-6-amine

HRID 527777
ノート
印刷プレビュー

反応式

HRID 527777 の反応式
F[C:2](F)(F)[C:3](O)=O.[CH2:8]([O:12][C:13]1[NH:14][C:15]([NH2:24])=[C:16]2[C:20]([N:21]=1)=[N:19][C:18]([O:22][CH3:23])=[N:17]2)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].BrCCCBr.N1CCC1.[CH2:40]([N:42]([CH2:45][CH3:46])[CH2:43]C)C>CN(C=O)C>[N:42]1([CH2:40][CH2:2][CH2:3][N:19]2[C:18]([O:22][CH3:23])=[N:17][C:16]3[C:20]2=[N:21][C:13]([O:12][CH2:8][CH2:9][CH2:10][CH3:11])=[N:14][C:15]=3[NH2:24])[CH2:43][CH2:46][CH2:45]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 80011,3-DibromopropaneHCID 8471TriethylamineHCID 10422AzetidineHCID 11430Potassium CarbonateHCID 178450357HCID 178450357、化合物

生成物 1

HCID 592526009-[3-(1-Azetidinyl)propyl]-2-(butyloxy)-8-(methyloxy)-9H-purin-6-amine収率 13.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
50 °C

実験手順

2-(Butyloxy)-8-(methyloxy)-1H-purin-6-amine trifluoroacetate (100 mg, 0.285 mmol) was dissolved in DMF (1 ml) and potassium carbonate (98 mg, 0.712 mmol) was added. The reaction mixture was stirred at 50° C. under nitrogen for 1 hour and then cooled to room temperature. 1,3-Dibromopropane (0.029 ml, 0.285 mmol) was added and after stirring for a further 40 mins. azetidine (0.038 ml, 0.569 mmol) and triethylamine (0.079 ml, 0.569 mmol) in DMF (1 ml) were added. The reaction mixture was then stirred for a further 18 hours. The solvent was removed and the residue was partitioned between dichloromethane (2 ml) and water (2 ml). The layers were separated using a hydrophobic frit and the aqueous phase was re-extracted with DCM (2 ml). The combined organic extracts were concentrated and the residue was dissolved in 1:1 MeOH:DMSO (1 ml) and purified by MDAP (Method A). The product containing fractions were evaporated under a stream of nitrogen to give the title compound as a white solid (13 mg).

後処理

  1. temperaturecooled to room temperature
  2. stirringafter stirring for a further 40 mins
  3. stirringThe reaction mixture was then stirred for a further 18 hours
  4. customThe solvent was removed
  5. customthe residue was partitioned between dichloromethane (2 ml) and water (2 ml)
  6. customThe layers were separated
  7. extractionthe aqueous phase was re-extracted with DCM (2 ml)
  8. concentrationThe combined organic extracts were concentrated
  9. dissolutionthe residue was dissolved in 1:1 MeOH
  10. customDMSO (1 ml) and purified by MDAP (Method A)
  11. additionThe product containing fractions
  12. customwere evaporated under a stream of nitrogen

出典と根拠

ORDレコード
ord-404d62603cb143eb8d9cd68f29be3223
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09346806B2

反応ノート

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