Triethylamine → 4-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one

HRID 1847050Notes

Reaction equation

HRID 1847050 reaction equation
[OH:1][CH:2]([CH2:17][OH:18])[CH2:3][N:4]1[C:9](=[O:10])[CH:8]=[N:7][C:6]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[N:14][C:5]1=2.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].C(N(CC)CC)C.O.C(=O)(O)[O-].[Na+]>ClCCl.CN(C)C1C=CN=CC=1>[Si:19]([O:18][CH2:17][CH:2]([OH:1])[CH2:3][N:4]1[C:9](=[O:10])[CH:8]=[N:7][C:6]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[N:14][C:5]1=2)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 670297844-(2,3-Dihydroxypropyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneHCID 86585896Sodium bicarbonate water

Product 1

HCID 867249764-(3-{[tert-Butyl(dimethyl)silyl]oxy}-2-hydroxypropyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-oneYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (30 ml) was dissolved 4-(2,3-dihydroxypropyl)-6-methoxypyrido[2,3-b]pyrazin-3(4H)-one (1.34 g, 5.32 mmol). To the solution were added tert-butyldimethylsilyl chloride (882 mg, 5.85 mmol), triethylamine (0.96 ml, 6.92 mmol) and 4-dimethylamino pyridine (130 mg, 1.06 mmol) under cooling on ice and the reaction mixture was stirred for 15 hours while the temperature was raised to room temperature. Saturated sodium bicarbonate water was added to the reaction solution, which was extracted with dichloromethane and the extract was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to yield 1.35 g (70%) of the title compound in the form of a white solid.

Workup

  1. temperatureunder cooling on ice
  2. extractionwas extracted with dichloromethane
  3. dry with materialthe extract 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-4ab4de970a8e474ca20a8950ca5380b5
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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