Sodium Hydroxide → 2-(1-bromopropyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 58223

반응식

HRID 58223 반응식
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[Br:9][CH:10]([CH2:18][CH3:19])[C:11](=O)[CH2:12][C:13](OC)=[O:14].[OH-].[Na+]>>[Br:9][CH:10]([C:11]1[N:8]=[C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]2[C:13](=[O:14])[CH:12]=1)[CH2:18][CH3:19]

참가 물질

4

반응물 3

HCID 14798Sodium HydroxideHCID 157652-Amino-6-methylpyridineHCID 86650061Methyl 4-bromo-3-oxohexanoate

생성물 1

HCID 668642082-(1-bromopropyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one수율 64.8%

반응 조건

온도
110 °C

실험 절차

To a manually stirred polyphosphoric acid (80 g, 800 mmol) in a 1000 mL beaker at room temperature was added 6-methyl-2-pyridinamine (15 g, 140 mmol), followed by methyl 4-bromo-3-oxohexanoate (37.3 g, 167 mmol). The mixture was heated with stirring at 110° C. for 5 h. After cooling, the dark slurry was transferred into 300 g of ice. The pH of the mixture was adjust to 6-7 with 10% sodium hydroxide. The precipitate was collected by filtration under reduced pressure, washed with water, and air dried to yield the desired product (25.4 g, 64.8%). LCMS calculated for C12H14BrN2O (M+H)+: m/z=281.0. Found: 281.2. 1H NMR (DMSO-d6, 300 MHz) δ 7.66 (1H, d, J=9.0 and 6.9 Hz), 7.39 (1H, d, J=9.0 Hz), 6.90 (1H, d, J=6.9 Hz), 6.33 (1H, s), 4.91 (1H, t, J=7.5 Hz), 2.91 (3H, s), 2.15 (2H, qd, J=7.5 and 7.5 Hz), 0.93 (3H, t, J=7.5 Hz) ppm.

후처리

  1. temperatureThe mixture was heated
  2. temperatureAfter cooling
  3. filtrationThe precipitate was collected by filtration under reduced pressure
  4. washwashed with water, and air
  5. customdried

출처 및 근거

ORD 기록
ord-72a6a95511a64b5db4c3ad6114719f9e
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434746B2

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