3-Furanol, tetrahydro- → 3,6-Dimethyl-4-(tetrahydrofuran-3-yloxy)-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridine

HRID 1067270노트

반응식

HRID 1067270 반응식
[H-].[Na+].[OH:3][CH:4]1[CH2:8][CH2:7][O:6][CH2:5]1.Cl[C:10]1[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]2[N:17]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])[N:18]=[C:19]([CH3:20])[C:11]=12>CCCCCC.O1CCCC1>[CH3:20][C:19]1[C:11]2[C:12](=[N:13][C:14]([CH3:16])=[CH:15][C:10]=2[O:3][CH:4]2[CH2:8][CH2:7][O:6][CH2:5]2)[N:17]([C:21]2[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[CH3:29])[N:18]=1

참가 물질

6

반응물 3

HCID 99603-Furanol, tetrahydro-HCID 24758Sodium hydrideHCID 211929064-chloro-3,6-dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridine

생성물 1

HCID 224526183,6-Dimethyl-4-(tetrahydrofuran-3-yloxy)-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

Sodium hydride (60% in oil, 176 mg, 4.4 mmol) was washed with hexane and suspended in 2 ml of tetrahydrofuran. 3-Hydroxytetrahydrofuran (1 ml) was added and stirred at room temperature for 5 minutes. A solution of 4-chloro-3,6-dimethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazolo[3,4-b]pyridine (200 mg, 0.665 mmol) in 1 ml of THF was added and the resulting mixture was heated at reflux for 8 hours. The mixture was quenched with water and extracted with EtOAc. The organic layer was dried and concentrated to give 334 mg of crude product. The crude material was purified through silica gel column chromatography using 1% methanol in chloroform as eluent to give 127 mg of a beige solid, mp 117-119° C.; IR(KBr) 2950, 1600, 1580 cm−1; high MS, calc. 351.1941, found, 351.19386; 1H NMR (CDCl3): 6.90 (s, 2H), 6.15 (s, 1H), 5.07 (m, 1H), 3.9-4.05 (m, 4H), 2.6 (s, 3H), 2.47 (s, 3H), 2.38 (s, 3H), 2.2-2.3 (m, 2H), 1.98 (s, 3H), 1.96 (s, 3H) ppm.

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 8 hours
  3. customThe mixture was quenched with water
  4. extractionextracted with EtOAc
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customto give 334 mg of crude product
  8. customThe crude material was purified through silica gel column chromatography

출처 및 근거

ORD 기록
ord-36e248f9fdb044379fe9c98858efddc2
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248753B1

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