Potassium Carbonate → 6-(3-cyclopropyl-3-fluoroazetidin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylsulfonyl)pyrimidin-4-amine

HRID 1091824

反応式

HRID 1091824 の反応式
[CH:1]1([C:4]2([F:23])[CH2:7][N:6]([C:8]3[N:13]=[C:12](SC)[N:11]=[C:10]([NH:16][C:17]4[NH:21][N:20]=[C:19]([CH3:22])[CH:18]=4)[CH:9]=3)[CH2:5]2)[CH2:3][CH2:2]1.O[O:25][S:26]([O-:28])=O.[K+].OS([O-])=O.[Na+].[C:35]([O-])([O-])=O.[K+].[K+]>CO.O>[CH:1]1([C:4]2([F:23])[CH2:7][N:6]([C:8]3[N:13]=[C:12]([S:26]([CH3:35])(=[O:28])=[O:25])[N:11]=[C:10]([NH:16][C:17]4[NH:21][N:20]=[C:19]([CH3:22])[CH:18]=4)[CH:9]=3)[CH2:5]2)[CH2:2][CH2:3]1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 23665763Sodium BisulfiteHCID 23707502Potassium hydroxy sulfiteHCID 178503490HCID 178503490、化合物

生成物 1

HCID 1784282456-(3-cyclopropyl-3-fluoroazetidin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylsulfonyl)pyrimidin-4-amine

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of 6-(3-cyclopropyl-3-fluoroazetidin-1-yl)-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylthio)pyrimidin-4-amine (130 g, 389 mmol) in MeOH (5.2 L) was cooled to 0° C. A solution of oxone (526 g, 855 mmol) in H2O (5.2 L) was slowly added to the slurry keeping the temperature below 5° C. After addition the reaction was allowed to warm to room temperature overnight. A 10% solution of NaHSO3 (325 ml) and a 10% solution of K2CO3 (2.6 L) was then added to neutralize the reaction mixture, the solution filtered and the filter cake washed with H2O (3.3 L). The solid was slurried in H2O (2.6 L), the solution filtered and the filter cake washed with H2O (3.3 L). The solid was dried under vacuum (72.3 g, 51%). 1H NMR (DMSO): 0.47 (2H, m), 0.60 (2H, m), 1.43-1.46 (1H, m), 2.20 (3H, s), 3.25 (3H, s), 3.97-4.11 (4H, m), 5.93 (1H, br s), 6.47 (1H, br s). 9.88 (1H, s), 12.01 (1H, br s). ES+ 367

後処理

  1. customthe temperature below 5° C
  2. additionAfter addition the reaction
  3. filtrationthe solution filtered
  4. washthe filter cake washed with H2O (3.3 L)
  5. filtrationthe solution filtered
  6. washthe filter cake washed with H2O (3.3 L)
  7. customThe solid was dried under vacuum (72.3 g, 51%)

出典と根拠

ORDレコード
ord-d3bc4d9a208f4c24b398424854fd084d
出典データセット
uspto-grants-2012_03
特許番号
US08129399B2

関連ノート

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