Triphenylphosphine → 5-(Quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizine-4,8-diamine

HRID 336142노트

반응식

HRID 336142 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH:23]1[CH2:31][CH2:30][C:29]2[N:25]([C:26]3[N:45]=[CH:44][N:43]=[C:42]([NH2:46])[C:27]=3[C:28]=2[C:32]2[CH:33]=[N:34][C:35]3[C:40]([CH:41]=2)=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:24]1)=[N+]=[N-]>C1COCC1.O>[N:34]1[C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:41]=[C:32]([C:28]2[C:27]3[C:42]([NH2:46])=[N:43][CH:44]=[N:45][C:26]=3[N:25]3[C:29]=2[CH2:30][CH2:31][CH:23]([NH2:20])[CH2:24]3)[CH:33]=1

참가 물질

5

반응물 2

HCID 11776TriphenylphosphineHCID 867112828-Azido-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-4-amine

생성물 1

HCID 867112835-(Quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizine-4,8-diamine수율 72.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Polymer-supported triphenylphosphine (˜3.0 mmol/g, 1.42 g) was added to a solution of 8-azido-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-4-amine (508 mg) obtained in Step 10 in THF (10 ml) and water (1 ml) at room temperature. The reaction mixture was heated under reflux for 1 hour. After cooling, the reaction mixture was filtered through Celite, washed with ethanol, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol) to obtain the title compound as a yellow solid (342 mg). ESI-MS m/z 331 (MH+).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through Celite
  5. washwashed with ethanol
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol)

출처 및 근거

ORD 기록
ord-e77d0a431a3e47db8ab28845288912c9
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889666B2

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