Indoline → 4-(2,3-Dihydro-1H-indol-1-yl)-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 369703

반응식

HRID 369703 반응식
Cl[C:2]1[C:3]2[C:10]([CH3:11])=[C:9]([CH3:12])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1>C(O)CCC>[N:13]1([C:2]2[C:3]3[C:10]([CH3:11])=[C:9]([CH3:12])[NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1

참가 물질

4

반응물 2

HCID 10328IndolineHCID 130411444-chloro-5,6-dimethyl-7H-pyrrolo(2,3-d)pyrimidine

생성물 1

HCID 232824634-(2,3-Dihydro-1H-indol-1-yl)-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidine

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

Under an argon atmosphere, 0.2 g (1.1 mmol) of 4-chloro-5,6-dimethyl-7H-pyrrolo[2,3-d]-pyrimidine (see Liebigs Ann. Chem. 1986(9), 1485-1505; CAS-Reg. No. 82703-38-6) and 0.15 ml (1.32 mmol) of 2,3-dihydroindole (Fluka, Buchs, Switzerland) in 5 ml of abs. n-butanol are heated at reflux for 2 hours until the starting material is no longer present in TLC. The reaction mixture is concentrated by evaporation in vacuo at 50° C. The brown residue is dissolved in 30 ml of ethyl acetate, and 10 ml of 1 N NaOH solution are added. The organic phase is separated off and washed three times with a small amount of water, dried and concentrated by evaporation. The crude product is dissolved in 10 ml of THF, and n-hexane is added until crystallization begins. Stirring is carried out at 0° C. and the product is filtered off with suction and dried under a high vacuum. Pure 4-(2,3-dihydroindol-1-yl)-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidine is obtained in the form of colorless crystals having a melting point of 220-221° C. FAB-MS: (M+H)+ =265 (corresponds to C16H16N4); Rf value (toluene-acetone--4:6)=0.46.

후처리

  1. temperatureat reflux for 2 hours until the starting material
  2. concentrationThe reaction mixture is concentrated by evaporation in vacuo at 50° C
  3. dissolutionThe brown residue is dissolved in 30 ml of ethyl acetate
  4. addition10 ml of 1 N NaOH solution are added
  5. customThe organic phase is separated off
  6. washwashed three times with a small amount of water
  7. customdried
  8. concentrationconcentrated by evaporation
  9. dissolutionThe crude product is dissolved in 10 ml of THF
  10. additionn-hexane is added until crystallization
  11. customis carried out at 0° C.
  12. filtrationthe product is filtered off with suction
  13. customdried under a high vacuum

출처 및 근거

ORD 기록
ord-9d986eb484564843b3a391ba6cd8482d
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140317

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