2-Pyridinamine, 5-bromo-6-methyl- → HCID 178469685、化合物

HRID 2120765ノート

反応式

HRID 2120765 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([Br:9])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13](=[C:17]([C:21]([O-])=O)[C:18]([O-])=[O:19])[O:14]CC)[CH3:11]>>[Br:9][C:5]1[CH:4]=[C:3]2[C:2](=[N:7][C:6]=1[CH3:8])[N:1]=[CH:21][C:17]([C:13]([O:12][CH2:10][CH3:11])=[O:14])=[C:18]2[OH:19]

参加物

3

反応物 2

HCID 1706782-Pyridinamine, 5-bromo-6-methyl-HCID 23435867Diethoxymethylenemalonate

生成物 1

HCID 178469685HCID 178469685、化合物収率 35%

反応条件

温度
250 °C

実験手順

A solution of 6-amino-3-bromo-2-methylpyridine (1.89 g, 10 mmol) and diethoxymethylenemalonate (2.16 g, 10 mmol) is heated at 110° C. for 30 min. The reaction is cooled and the residue is recrystallized from EtOH. To the resulting solid is dissolved in 45 mL of Ph2O. The mixture is heated to 250° C. for 3 h. The solution is then cooled to room temperature and the resulting precipitate is collected and dried. The crude product is chromatographed on silica (Biotage flash 40M, 2% MeOH/CH2Cl2 eluent). Fractions homogeneous by TLC are collected and concentrated to yield 1.075 g (35%) of the desired product as a yellow solid. Physical data are as follows: m.p. 270° C. (dec.); 1H NMR (DMSO-d6) δ12.73, 8.49, 8.47, 4.21, 2.67, 1.27.

後処理

  1. temperatureThe reaction is cooled
  2. customthe residue is recrystallized from EtOH
  3. dissolutionTo the resulting solid is dissolved in 45 mL of Ph2O
  4. temperatureThe solution is then cooled to room temperature
  5. customthe resulting precipitate is collected
  6. customdried
  7. customThe crude product is chromatographed on silica (Biotage flash 40M, 2% MeOH/CH2Cl2 eluent)
  8. customFractions homogeneous by TLC are collected
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-bd237a5b5dde41d791faaaa9bf5aa986
出典データセット
uspto-grants-2004_02
特許番号
US06693114B2

反応ノート

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