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

HRID 336142Notes

Reaction equation

HRID 336142 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-e77d0a431a3e47db8ab28845288912c9
Source dataset
uspto-grants-2014_11
Patent number
US08889666B2

Reaction notes

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