2-Methyl-4-methoxymethyl-5-cyano-6-oxypyridine → 3-(aminomethyl)-4-(methoxymethyl)-6-methyl-2(1H)-Pyridinone

HRID 516739ノート

反応式

HRID 516739 の反応式
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[C:4]([CH2:11][O:12][CH3:13])[CH:3]=1>C(O)(=O)C.[Ni]>[NH2:10][CH2:9][C:5]1[C:6](=[O:8])[NH:7][C:2]([CH3:1])=[CH:3][C:4]=1[CH2:11][O:12][CH3:13]

参加物

4

反応物 1

HCID 949992-Methyl-4-methoxymethyl-5-cyano-6-oxypyridine

生成物 1

HCID 552557633-(aminomethyl)-4-(methoxymethyl)-6-methyl-2(1H)-Pyridinone

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 176Acetic Acid溶媒

実験手順

6-Methyl-4-[(methyloxy)methyl]-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (1.000 g, 5.61 mmol) was suspended in acetic acid (150 ml) and the solution passed through an H-cube instrument equipped with Raney-Ni cartridge at a rate of 1 mL/min at 50 psi and 60° C. After 18 h. the acetic acid was removed under reduced pressure and the remaining residue was dissolved in MeOH. The methanolic solution was passed through a 0.2 μm teflon syringe filter. The methanolic filtrate was purified by reverse phase HPLC (Gemini 50×100 5 μm column. Run 1: 3 min, 90-10%. Run 2, 5 min 0-10%. Run 3, 10 min, 0-20%. The product fractions were concentrated to dryness on a Genevac HT-4 instrument to afford 3-(aminomethyl)-6-methyl-4-[(methyloxy)methyl]-2(1H)-pyridinone as a pale grey waxy solid (900 mg, 70.2% yield) LCMS MH+=183.0 1H NMR (400 MHz, DMSO-d6) δ 8.40 (br. s., 1H), 6.10 (s, 1H), 4.39 (s, 2H), 3.66 (br. s., 2H), 3.32 (s, 3H), 2.19 (s, 3H).

後処理

  1. customAfter 18 h. the acetic acid was removed under reduced pressure
  2. dissolutionthe remaining residue was dissolved in MeOH
  3. filtrationfilter
  4. customThe methanolic filtrate was purified by reverse phase HPLC (Gemini 50×100 5 μm column
  5. custom3 min, 90-10%
  6. custom2, 5 min 0-10%
  7. custom3, 10 min, 0-20%
  8. concentrationThe product fractions were concentrated to dryness on a Genevac HT-4 instrument

出典と根拠

ORDレコード
ord-4714b5308a4243c3946350022cdd74ba
出典データセット
uspto-grants-2015_08
特許番号
US09114141B2

反応ノート

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