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Sodium Thiosulfate → Methyl 2-(methylsulfonyl)pyrimidine-5-carboxylate

HRID 219671
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HRID 219671 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8](SC)=[N:9][CH:10]=1)=[O:4].[CH:13]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:24][S:25]([O-:28])(=S)=O.[Na+].[Na+]>C(Cl)Cl.O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([S:25]([CH3:13])(=[O:28])=[O:24])=[N:7][CH:6]=1)=[O:4]
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참가 물질

6

반응물 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 11194721Methyl 2-(Methylthio)pyrimidine-5-carboxylate

생성물 1

HCID 53396491Methyl 2-(methylsulfonyl)pyrimidine-5-carboxylate수율 90%

시약·촉매·용매 2

HCID 962Water용매HCID 6344
Dichloromethane
용매

실험 절차

To a solution of 2-methylsulfanyl-pyrimidine-5-carboxylic acid methyl ester 1 (1 g, 5.43 mmol) in DCM (60 mL) is added MCPBA (2.81 g, 16.29 mmol) portion wise at room temperature. The resulting solution is stirred at room temperature overnight. A solution of Na2S2O3 (1.6 g) in water (60 mL) is added. The mixture is stirred at room temperature for 20 min. The layer is separated, and the water layer is extracted with DCM (2×20 mL). The combined DCM layer is washed with saturated NaHCO3 (3×20 mL), dried (Na2SO4), filtered and concentrated in vacuo to afford 2-methanesulfonyl-pyrimidine-5-carboxylic acid methyl ester as a solid (1.05 g, 90%). MS: 217 (M+H); 1H NMR (300 MHz, CDCl3): δ 3.41 (s, 3H), 4.06 (s, 3H), 9.44 (s, 2H).

후처리

  1. stirringThe mixture is stirred at room temperature for 20 min
  2. customThe layer is separated
  3. extractionthe water layer is extracted with DCM (2×20 mL)
  4. washThe combined DCM layer is washed with saturated NaHCO3 (3×20 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-bab0c6a785ff4f04be7cf4774c1a7229
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202863B2

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