Sodium Sulfite → 8-Cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 12351

Reaction equation

HRID 12351 reaction equation
[CH:1]1C=C(Cl)C=C(C(OO)=O)C=1.[CH2:12]([O:14][C:15]([C:17]1[C:18](=[O:35])[C:19]2[CH:24]=[N:23][C:22](SC)=[N:21][C:20]=2[N:27]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH:28]=1)=[O:16])[CH3:13].[O-:36][S:37]([O-:39])=O.[Na+].[Na+]>ClCCl>[CH2:12]([O:14][C:15]([C:17]1[C:18](=[O:35])[C:19]2[CH:24]=[N:23][C:22]([S:37]([CH3:1])(=[O:39])=[O:36])=[N:21][C:20]=2[N:27]([CH:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)[CH:28]=1)=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 685832078-Cyclohexyl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Product 1

HCID 252234828-Cyclohexyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-CPBA (0.33 g, 1.5 mmol of a 70% w/w mixture) was added to a solution of 8-cyclohexyl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.206 g, 0.59 mmol) in dichloromethane (15 mL). After 2 hours, a 10% solution of Na2SO3 (1 mL) was added and the mixture was partitioned between sat. NaHCO3 and dichloromethane. The organic layer was dried (MgSO4) and concentrated to provide 0.22 g of the title compound. Mass Spectrum (LCMS, ESI pos.) Calcd. For C17H21N3O5S: 379.12. found: (M+H) 380.1.

Workup

  1. customthe mixture was partitioned between sat. NaHCO3 and dichloromethane
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1ac2aa84f60741819c22e5410f4c6a75
Source dataset
uspto-grants-2010_06
Patent number
US07728003B2

Linked notes

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