Phosgene → 6-(2-Furyl)-9-(1-pyrrolidinylcarbonyl)-9H-purine-2-amine

HRID 271259

反応式

HRID 271259 の反応式
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6](Cl)(Cl)=[O:7].[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]1[NH:23][C:22]([NH2:24])=[N:21][C:20]2[C:16]=1[N:17]=[CH:18][N:19]=2.CCN(CC)CC>C1(C)C=CC=CC=1.O>[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]1[N:23]=[C:22]([NH2:24])[N:21]=[C:20]2[C:16]=1[N:17]=[CH:18][N:19]2[C:6]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:7]

参加物

7

反応物 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 31268PyrrolidineHCID 1785082476-(furan-2-yl)-9H-purin-2-amine

生成物 1

HCID 598349776-(2-Furyl)-9-(1-pyrrolidinylcarbonyl)-9H-purine-2-amine収率 62%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒2 回

反応条件

温度
80 °C

実験手順

A solution of pyrrolidine (50 mL, 0.6 mmol) in toluene (2 mL) was treated with a solution of phosgene in toluene (0.31 mL, 1.93-M, 0.6 mmol), heated at 80° C. for 30 mins, cooled and concentrated in vacuo. The residue was dissolved in THF (2 mL) and added to a solution of 6-(2-furyl)-1H-purine-2-amine (100 mg, 0.5 mmol) and Et3N (83 mL, 0.6 mmol) in DMP (0.5 mL), stirred at 60° C. for 16 h, poured into water and extracted with EtOAc. The combined organic phase was dried (MgSO4), concentrated in vacuo and the resulting solid triturated with EtOAc/heptane and filtered to give the title compound (92 mg, 62%) as a cream solid.

後処理

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in THF (2 mL)
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe resulting solid triturated with EtOAc/heptane
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-aa7f95a0fb27463884a087d55b99382d
出典データセット
uspto-grants-2008_11
特許番号
US07452894B2

関連ノート

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