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

HRID 1847050ノート

反応式

HRID 1847050 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4ab4de970a8e474ca20a8950ca5380b5
出典データセット
uspto-grants-2015_02
特許番号
US08952010B2

反応ノート

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