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

HRID 58218

반응식

HRID 58218 반응식
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[Cl:9][CH:10]([CH3:18])[C:11](=O)[CH2:12][C:13](OC)=[O:14].[OH-].[Na+]>>[Cl: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)[CH3:18]

참가 물질

4

반응물 3

HCID 14798Sodium HydroxideHCID 157652-Amino-6-methylpyridineHCID 22068615Methyl 4-chloro-3-oxopentanoate

생성물 1

HCID 668634172-(1-chloroethyl)-6-methyl-4H-pyrido[1,2-a]pyrimidin-4-one수율 33%

반응 조건

온도
110 °C

실험 절차

To a manually stirred polyphosphoric acid (30 g, 200 mmol) in a 200 mL beaker was added 6-methyl-2-pyridinamine (Aldrich, 4.7 g, 43 mmol), followed by methyl 4-chloro-3-oxopentanoate (8.584 g, 52.15 mmol). The mixture was heated with stirring at 110° C. for 5 h. After being cooled, the dark slurry was transferred on to 100 g of ice. The pH of the mixture was adjusted to 6-7 with 10% sodium hydroxide. The mixture was extracted with methylene chloride. The combined organic layers were washed with water, brine, dried over magnesium sulfate and evaporated to dryness. The residue was purified on silica gel, eluting with 0-10% methanol in methylene chloride, to yield the desired product (3.16 g, 32.7%). LCMS calculated for C11H12ClN2O (M+H)+: m/z=223.1. Found: 223.2.

후처리

  1. temperatureThe mixture was heated
  2. temperatureAfter being cooled
  3. extractionThe mixture was extracted with methylene chloride
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified on silica gel
  8. washeluting with 0-10% methanol in methylene chloride

출처 및 근거

ORD 기록
ord-e572b17928984445aef67dc3ffcc65ac
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434746B2

연결된 노트

불러오는 중…