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

HRID 336142ノート

反応式

HRID 336142 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-e77d0a431a3e47db8ab28845288912c9
出典データセット
uspto-grants-2014_11
特許番号
US08889666B2

反応ノート

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