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

HRID 1989025Notes

Reaction equation

HRID 1989025 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:34])[C:19]2[CH:24]=[N:23][C:22](SC)=[N:21][C:20]=2[N:27]([CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[CH:28]=1)=[O:16])[CH3:13].[O-:35][S:36]([O-:38])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:12]([O:14][C:15]([C:17]1[C:18](=[O:34])[C:19]2[CH:24]=[N:23][C:22]([S:36]([CH3:1])(=[O:38])=[O:35])=[N:21][C:20]=2[N:27]([CH:29]2[CH2:30][CH2:31][CH2:32][CH2:33]2)[CH:28]=1)=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 686785918-Cyclopentyl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Product 1

HCID 686792108-Cyclopentyl-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 (0.45 g, 2.05 mmol of a 77% powder) was added to a solution of 8-cyclopentyl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.27 g, 0.82 mmol) in DCM (5 mL). After 2 hours, a 10% solution of Na2SO3 (2 mL) was added and the mixture was partitioned between sat. NaHCO3 and DCM. The organic layer was dried (MgSO4) and concentrated to provide the title compound. Mass Spectrum (LCMS, ESI pos.) Calcd. For C16H19N3O5S: 365.10, found: (M+H) 366.1.

Workup

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

Sources & evidence

ORD record
ord-92099b7490ba46f5a1eacf62e929a6c9
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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