2-(Benzenesulfonyl)-3-phenyloxaziridine → 3-(2,6-Difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

HRID 459962Notes

Reaction equation

HRID 459962 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[C:4]([F:12])[C:3]=1[N:13]1[CH2:22][C:21]2[C:16](=[N:17][C:18]([S:23][CH3:24])=[N:19][CH:20]=2)[N:15]([CH2:25][CH3:26])[C:14]1=[O:27].C1(C2[O:36]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C(Cl)(Cl)Cl>[F:12][C:4]1[C:5]([O:10][CH3:11])=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[C:3]=1[N:13]1[CH2:22][C:21]2[C:16](=[N:17][C:18]([S:23]([CH3:24])=[O:36])=[N:19][CH:20]=2)[N:15]([CH2:25][CH3:26])[C:14]1=[O:27]

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 184447933-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfanyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

Product 1

HCID 184447943-(2,6-Difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfinyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 4.23 g (10.67 mmol) of 3-(2,6-difluoro-3,5-dimethoxy-phenyl)-1-ethyl-7-methylsulfanyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidin-2-one in 90 mL of chloroform was treated with 3.35 g (12.80 mmol) of 3-phenyl-2-(phenylsulfonyl)-oxaziridine and stirred at room temp. under N2 atmosphere overnight. Crude product was purified by medium-pressure chromatography eluting with straight ethyl acetate and a gradient of 1% to 3% MeOH in chloroform to give 4.45 g (quantitative) title compound. MS (APCI) (m+1)/z 413.1.

Workup

  1. customCrude product was purified by medium-pressure chromatography
  2. washeluting with straight ethyl acetate

Sources & evidence

ORD record
ord-4e846f77573b4c00beb61a61e2a7c304
Source dataset
uspto-grants-2007_03
Patent number
US07196090B2

Reaction notes

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