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

HRID 1847050노트

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HRID 1847050 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4ab4de970a8e474ca20a8950ca5380b5
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952010B2

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