Sodium Sulfite → HCID 68679511, compound

HRID 1989086Notes

Reaction equation

HRID 1989086 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:17][N:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]2[N:10]=[C:11](SC)[N:12]=[CH:13][C:8]=2[C:7]1=[O:25])=[O:5])[CH3:2].[CH:26]1C=C(Cl)C=C(C(OO)=O)C=1.[O-:37][S:38]([O-:40])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:25])[C:8]2[CH:13]=[N:12][C:11]([S:38]([CH3:26])(=[O:40])=[O:37])=[N:10][C:9]=2[N:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 68677843HCID 68677843, compound

Product 1

HCID 68679511HCID 68679511, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Benzyl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.39 g, 1.1 mmol) and m-CPBA (0.61 g (77% w/w), 2.7 mmol) were combined in DCM (20 mL). After 2 hours, a 10% solution of Na2SO3 (5 mL) was added and the mixture was partitioned between sat. NaHCO3 and DCM. The organic layer was dried (MgSO4) and concentrated. Chromatography on silica (25-100% EtOAc/hexanes gradient) provided 0.21 g of 8-benzyl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester. 1H NMR (400 MHz, CDCl3) δ (ppm): 9.70 (s, 1H), 8.72 (s, 1H), 7.38-7.41 (m, 5H), 5.57 (s, 2H), 4.40 (q, 2H, J=7.1 Hz), 3.38 (s, 3H), 1.40 (t, 3H, J=7.1 Hz).

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-d6a46e0059f546d8a90cd0327656aee2
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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