Cesium carbonate → 4-Chloro-5-((tetrahydrofuran-2-yl)methyl)-5H-pyrrolo[3,2-d]pyrimidine

HRID 1925990노트

반응식

HRID 1925990 반응식
[Cl:1][C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][O:20]1>CN(C)C=O.O>[Cl:1][C:2]1[C:3]2[N:10]([CH2:18][CH:19]3[CH2:23][CH2:22][CH2:21][O:20]3)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

생성물 1

HCID 735546514-Chloro-5-((tetrahydrofuran-2-yl)methyl)-5H-pyrrolo[3,2-d]pyrimidine수율 86.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (150 mg) in N,N-dimethylformamide (1.0 mL) was added cesium carbonate (478 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 2-(bromomethyl)tetrahydrofuran (242 mg), and the mixture was stirred at room temperature for 26 hrs. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (30 mL×3). The organic layer was washed with saturated brine (30 mL×3) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (silica gel, eluent:hexane/ethyl acetate=90/10→20/80). The object fraction was concentrated under reduced pressure and dried to give the title compound (200 mg) as a colorless oil.

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 26 hrs
  3. extractionextracted with ethyl acetate (30 mL×3)
  4. washThe organic layer was washed with saturated brine (30 mL×3)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. concentrationThe object fraction was concentrated under reduced pressure
  8. customdried

출처 및 근거

ORD 기록
ord-11141ae7736347c59f6cb0f9438656ed
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178543B2

반응 노트

불러오는 중…