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

HRID 271259

반응식

HRID 271259 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aa7f95a0fb27463884a087d55b99382d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452894B2

연결된 노트

불러오는 중…