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

HRID 58218

反応式

HRID 58218 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e572b17928984445aef67dc3ffcc65ac
出典データセット
uspto-grants-2016_09
特許番号
US09434746B2

関連ノート

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