Toluene → [4-(4-Fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)pyrimidin-5-yl]methanol

HRID 253045ノート

反応式

HRID 253045 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14](OC)=[O:15])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=[C:10]([S:21][CH3:22])[N:9]=2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14][OH:15])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=[C:10]([S:21][CH3:22])[N:9]=2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 1140TolueneHCID 11652673Methyl 4-(4-Fluorophenyl)-6-isopropyl-2-(methylthio)pyrimidine-5-carboxylate2 回HCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 29980411[4-(4-Fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)pyrimidin-5-yl]methanol収率 88%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

20 g (62.5 mmol) of methyl 4-(4′-fluorophenyl)-6-isopropyl-2-methylthio-pyrimidin-5-yl-carboxylate (10) and 300 mL of dry anhydrous toluene were loaded in a IL three-neck round bottomed flask, equipped with a mechanical stirrer and an air duct, and stirred under a nitrogen atmosphere. 100 mmol of diisobutyl aluminum hydride (DIBAI-H) was then added in batches into the mixture while cooling in an ice-salt bath. After TLC assay showed that the starting compound (10) was depleted, the reaction mixture was warmed up to room temperature and further reacted for 2-3 hours. 500 mL of water was then added, and the organic layer was collected, washed with water (200 mL×2) and a saturated solution of sodium chloride (200 mL×1), and then dried overnight over anhydrous magnesium sulfate. The mixture was then filtered, evaporated under reduced pressure to remove the solvent, and recrystallized in ethyl acetate, obtaining 16 g of a white crystal, yield 88%.

後処理

  1. customequipped with a mechanical stirrer
  2. temperaturewhile cooling in an ice-salt bath
  3. customfurther reacted for 2-3 hours
  4. customthe organic layer was collected
  5. washwashed with water (200 mL×2)
  6. dry with materiala saturated solution of sodium chloride (200 mL×1), and then dried overnight over anhydrous magnesium sulfate
  7. filtrationThe mixture was then filtered
  8. customevaporated under reduced pressure
  9. customto remove the solvent
  10. customrecrystallized in ethyl acetate

出典と根拠

ORDレコード
ord-7257b2d4602b46a994bc0a277aa5b486
出典データセット
uspto-grants-2011_01
特許番号
US07872012B2

反応ノート

読み込み中…