Tetrabutylammonium Fluoride → 4-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-ol

HRID 336139Notes

Reaction equation

HRID 336139 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH:27]1[CH2:35][CH2:34][C:33]2[N:29]([C:30]3[N:49]=[CH:48][N:47]=[C:46]([NH2:50])[C:31]=3[C:32]=2[C:36]2[CH:37]=[N:38][C:39]3[C:44]([CH:45]=2)=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:28]1)(C(C)(C)C)(C)C>C1COCC1>[NH2:50][C:46]1[C:31]2[C:32]([C:36]3[CH:37]=[N:38][C:39]4[C:44]([CH:45]=3)=[CH:43][CH:42]=[CH:41][CH:40]=4)=[C:33]3[N:29]([C:30]=2[N:49]=[CH:48][N:47]=1)[CH2:28][CH:27]([OH:26])[CH2:35][CH2:34]3

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 867112798-(Tert-butyldimethylsilyloxy)-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-4-amine

Product 1

HCID 867112804-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-olYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1 M tetrabutylammonium fluoride in THF (2.09 ml) was added to a solution of 8-(tert-butyldimethylsilyloxy)-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-4-amine (778 mg) obtained in Step 7 in THF (20 ml) at room temperature. The mixture was stirred at the same temperature for 1 hour, and the solvent was distilled off under reduced pressure. The resulting residue was treated with a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then 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 light-yellow solid (580 mg).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionThe resulting residue was treated with a saturated aqueous ammonium chloride solution
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was then distilled off under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol)

Sources & evidence

ORD record
ord-b1b80aa84ade4785b99cccf30bf7e374
Source dataset
uspto-grants-2014_11
Patent number
US08889666B2

Reaction notes

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