HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 2381961
Notes
Print preview

Reaction equation

HRID 2381961 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-c2fbc95ae24245038e7ce9692163b307
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08258130B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes