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

HRID 599327노트

반응식

HRID 599327 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-b2a6801564cd4a7ab447414623b97176
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07897762B2

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