Aluminium lithium hydride → (6-(Methoxy(methyl)amino)-4-(methylamino)pyridin-3-yl)methanol

HRID 599327ノート

反応式

HRID 599327 の反応式
[CH3:1][O:2][N:3]([CH3:17])[C:4]1[CH:14]=[C:13]([NH:15][CH3:16])[C:7]([C:8](OCC)=[O:9])=[CH:6][N:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][N:3]([CH3:17])[C:4]1[N:5]=[CH:6][C:7]([CH2:8][OH:9])=[C:13]([NH:15][CH3:16])[CH:14]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 86629461Ethyl 6-(methoxy(methyl)amino)-4-(methylamino)nicotinate

生成物 1

HCID 86629462(6-(Methoxy(methyl)amino)-4-(methylamino)pyridin-3-yl)methanol収率 77.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl 6-(methoxy(methyl)amino)-4-(methylamino)nicotinate (6 g, 25 mmol) in THF (60 mL) at 0° C. was added LiAlH4 (1.9 g, 50.2 mmol) in portions under N2 atmosphere. After 20 min, the reaction was quenched by addition of water followed by aqueous 2N NaOH. The resultant suspension was filtered and the filtrate was concentrated in vacuo to afford (6-(methoxy(methyl)amino)-4-(methylamino)pyridin-3-yl)methanol (3.8 g, 77.6% yield), which was used without further purification. 1H NMR (400 MHz, DMSO-d6): δ 7.61 (s, 1 H), 6.08 (s, 1 H), 5.86 (m, 1 H), 4.88 (t, J=5.2 Hz, 1 H), 4.30 (d, J=5.2 Hz, 2 H), 3.64 (s, 3 H), 3.04 (s, 3 H), 2.73 (d, J=4.8 Hz, 3 H); MS (ESI) m/z: 198.2 (M+H+).

後処理

  1. customthe reaction was quenched by addition of water
  2. filtrationThe resultant suspension was filtered
  3. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-b2a6801564cd4a7ab447414623b97176
出典データセット
uspto-grants-2011_03
特許番号
US07897762B2

反応ノート

読み込み中…