Potassium hydroxy sulfite → 2-(methylsulfinyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 570706Notes

Reaction equation

HRID 570706 reaction equation
[CH3:1][S:2][C:3]1[N:4]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[CH:17][CH:16]=2)[C:5](=[O:14])[C:6]2[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:7]=2[N:8]=1.[OH:27]OS([O-])=O.[K+]>C(O)(=O)C.O>[CH3:1][S:2]([C:3]1[N:4]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]([F:24])([F:26])[F:25])=[CH:19][CH:20]=2)[C:5](=[O:14])[C:6]2[CH2:12][CH2:11][C:10](=[O:13])[NH:9][C:7]=2[N:8]=1)=[O:27]

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 866853682-(methylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Product 1

HCID 866853692-(methylsulfinyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-dioneYield 76.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2-(methylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-5,6-dihydropyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (2.1 g) in acetic acid (40 mL) was added a solution of oxone (registered mark) (4.02 g) in water (8 mL). The reaction mixture was stirred at room temperature for 2 hr, water was added thereto, and the precipitate was collected by filtration to give the title compound (1.68 g).

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-52da78d23bec489790e72e4d3030aa7e
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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