Tetrabutylammonium Fluoride → 4-[3-Hydroxy-2-(methoxymethoxy)propyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847052Notes

Reaction equation

HRID 1847052 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][CH:28]([O:43][CH2:44][O:45][CH3:46])[CH2:29][N:30]1[C:35](=[O:36])[CH:34]=[N:33][C:32]2[CH:37]=[CH:38][C:39]([O:41][CH3:42])=[N:40][C:31]1=2)(C(C)(C)C)(C)C>O1CCCC1.ClCCl>[OH:26][CH2:27][CH:28]([O:43][CH2:44][O:45][CH3:46])[CH2:29][N:30]1[C:35](=[O:36])[CH:34]=[N:33][C:32]2[CH:37]=[CH:38][C:39]([O:41][CH3:42])=[N:40][C:31]1=2

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 867249774-[3-{[tert-Butyl(dimethyl)silyl]oxy}-2-(methoxymethoxy)propyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

Product 1

HCID 867249784-[3-Hydroxy-2-(methoxymethoxy)propyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetrabutyl ammonium fluoride in 1M tetrahydrofuran (3.22 ml, 3.22 mmol) was added to a solution of 4-[3-{[tert-Butyl(dimethyl)silyl]oxy}-2-(methoxymethoxy)propyl]-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (1.02 g, 2.48 mmol) in tetrahydrofuran (15 ml) under cooling on ice and the mixture was stirred for 15 hours. The reaction solution was diluted with dichloromethane and washed with saturated sodium bicarbonate water. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol) to yield 637 mg (87%) of the title compound in the form of an orange oily product.

Workup

  1. temperatureunder cooling on ice
  2. washwashed with saturated sodium bicarbonate water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-a0cbeaaff40b4ee7a236f1d6e57fdcea
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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