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

HRID 1989000Notes

Reaction equation

HRID 1989000 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:27])[C:8]2[CH:13]=[N:12][C:11](SC)=[N:10][C:9]=2[N:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[CH2:23][CH2:22][CH2:21]3)[CH:17]=1)=[O:5])[CH3:2].Cl[C:29]1C=C(C=CC=1)C(OO)=O.[S:39]([O-:43])([O-])(=[O:41])=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:27])[C:8]2[CH:13]=[N:12][C:11]([S:39]([CH3:29])(=[O:43])=[O:41])=[N:10][C:9]=2[N:16]([C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[CH2:23][CH2:22][CH2:21]3)[CH:17]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 252228788-Indan-5-yl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Product 1

HCID 252229828-Indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl esterYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-indan-5-yl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.3 g, 0.79 mmol) in 5 mL of CH2Cl2, was added 3-chloroperoxybenzoic acid (m-CPBA, 69.5%, 431 mg, 1.73 mmol) portionwise. The solution was stirred at room temperature for 3 hours. An aqueous solution of 10% sodium thiosulfate was added to quench the reaction. After 30 minutes saturated sodium bicarbonate solution was added, and the aqueous solution was extracted by CH2Cl2. The combined CH2Cl2 solution was washed with brine and dried over Na2SO4. Removal of the solvent and chromatography on silica, eluting with EtOAc/hexanes (1:3-1:1.6, v/v) gave 0.22 g (67%) of the title compound as an off-white solid. 1H NMR (300 MHz, CDCl3) δ (ppm): 9.75 (s, 1H), 8.70 (s, 1H), 7.39 (d, J=7.8 Hz, 1H), 7.24 (s, 1H), 7.16 (d, J=7.8 Hz, 1H), 4.38 (q, 2H), 3.19 (s, 3H), 3.00 (m, 4H), 2.10(m, 2H), 1.40 (t, 3H).

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe aqueous solution was extracted by CH2Cl2
  4. washThe combined CH2Cl2 solution was washed with brine
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent and chromatography on silica
  7. washeluting with EtOAc/hexanes (1:3-1:1.6

Sources & evidence

ORD record
ord-9120ccf6b81d450a9627eee360bfd981
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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