2-Pyridinamine, 5-bromo-6-methyl- → HCID 178469685, 화합물

HRID 2120765노트

반응식

HRID 2120765 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

HCID 178469685HCID 178469685, 화합물수율 35%

반응 조건

온도
250 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bd237a5b5dde41d791faaaa9bf5aa986
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06693114B2

반응 노트

불러오는 중…