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

HRID 499093

반응식

HRID 499093 반응식
[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

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 23665763Sodium BisulfiteHCID 23707502Potassium hydroxy sulfiteHCID 178503490HCID 178503490, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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

후처리

  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%)

출처 및 근거

ORD 기록
ord-55052ea5a74f40d09cabf1409060c720
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07767672B2

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