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Ethanol → N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-(morpholinomethyl)pyridin-2-amine

HRID 1621413
ノート
印刷プレビュー

反応式

HRID 1621413 の反応式
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([NH:15][C:16]2[C:23]([C:24]3[N:29]=[C:28]([CH3:30])[N:27]=[C:26]([S:31][CH3:32])[N:25]=3)=[CH:22][C:19]([CH:20]=O)=[CH:18][N:17]=2)=[CH:11][CH:10]=1.CCO.C([BH3-])#N.[Na+]>CC(O)=O.O.CCOC(C)=O>[CH3:7][O:8][C:9]1[N:14]=[CH:13][C:12]([NH:15][C:16]2[C:23]([C:24]3[N:29]=[C:28]([CH3:30])[N:27]=[C:26]([S:31][CH3:32])[N:25]=3)=[CH:22][C:19]([CH2:20][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:18][N:17]=2)=[CH:11][CH:10]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 702EthanolHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 866470496-(6-Methoxypyridin-3-ylamino)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)nicotinaldehyde

生成物 1

HCID 66612061N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-(morpholinomethyl)pyridin-2-amine収率 63.7%

試薬・触媒・溶媒 3

HCID 176Acetic Acid触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Morpholine (0.018 mL, 0.204 mmol) and a few drops of AcOH (3.88 μL, 0.068 mmol) were added to a stirred suspension of 6-(6-methoxypyridin-3-ylamino)-5-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)nicotinaldehyde (25 mg, 0.068 mmol) in EtOH (3.00 mL, 51.4 mmol), the mixture was stirred at room temperature for 1 h, then treated with sodium cyanoborohydride (4.26 mg, 0.068 mmol) and stirred at room temperature overnight. The mixture was diluted with water and EtOAc (10 mL each). The separated aqueous layer was extracted with ethyl acetate (2×10 mL) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give crude product which was purified by flash column chromatography (ISCO CombiFlash®, Teledyne ISCO, Lincoln, Nebr., DCM to 10% DCM in MeOH) to give N-(6-methoxypyridin-3-yl)-3-(4-methyl-6-(methylthio)-1,3,5-triazin-2-yl)-5-(morpholinomethyl)pyridin-2-amine (19 mg, 0.043 mmol, 63.7% yield) as a yellow solid. LCMS (API-ES) m/z 440 (M+H)+.

後処理

  1. stirringstirred at room temperature overnight
  2. extractionThe separated aqueous layer was extracted with ethyl acetate (2×10 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude product which
  7. customwas purified by flash column chromatography (ISCO CombiFlash®, Teledyne ISCO, Lincoln, Nebr., DCM to 10% DCM in MeOH)

出典と根拠

ORDレコード
ord-7480d9e94a094933bc9a8462f6fa5815
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08772480B2

反応ノート

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