Methyl iodide → Ethyl 1,6,8-Trimethyl-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate

HRID 1070647

반응식

HRID 1070647 반응식
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([CH3:13])[N:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:19]([O-])([O-])=O.[Na+].[Na+].IC>CN(C=O)C>[CH3:19][N:5]1[C:6]2[C:11](=[CH:10][C:9]([CH3:12])=[N:8][C:7]=2[CH3:13])[C:2](=[O:1])[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 22397159Ethyl 4-Hydroxy-6,8-dimethyl-1,7-naphthyridine-3-carboxylate

생성물 1

HCID 22397181Ethyl 1,6,8-Trimethyl-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate수율 21%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Ethyl 4-hydroxy-6,8-dimethyl-1,7-naphthyridine-3-carboxylate (Preparation 47, 460 mg) is dissolved in DMF (30 mL) and treated with Na2CO3 (396 mg). Iodomethane (0.3 mL) is slowly added to the mixture, and it is then heated to reflux for 1 h. The reaction mixture is cooled to room temperature, quenched with water (20 mL) and extracted with CH2Cl2 (50 mL). The organic layer is separated, dried (MgSO4), and to concentrated in vacuo. The residue is purified by silica gel column chromatography (5% methanol/CH2Cl2) to give 100 mg (21%) of the title compound as a white solid. Physical characteristics: MS (ESI+) m/z 261 (M+H)+; 1H NMR (DMSO) δ8.61, 7.78, 4.23, 4.18, 3.00, 2.56, 1.28.

후처리

  1. temperatureis then heated
  2. temperatureto reflux for 1 h
  3. customquenched with water (20 mL)
  4. extractionextracted with CH2Cl2 (50 mL)
  5. customThe organic layer is separated
  6. dry with materialdried (MgSO4)
  7. concentrationto concentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography (5% methanol/CH2Cl2)

출처 및 근거

ORD 기록
ord-bd7cd7f746aa497b9fc42da9635b855a
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903097B2

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