2-(Benzenesulfonyl)-3-phenyloxaziridine → 8-cyclopropyl-2-methylsulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 586496Notes

Reaction equation

HRID 586496 reaction equation
[CH:1]1([N:4]2[C:9]3[N:10]=[C:11]([S:14][CH3:15])[N:12]=[CH:13][C:8]=3[CH:7]=[CH:6][C:5]2=[O:16])[CH2:3][CH2:2]1.C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:24])C=CC=CC=1>C(Cl)Cl>[CH:1]1([N:4]2[C:9]3[N:10]=[C:11]([S:14]([CH3:15])=[O:24])[N:12]=[CH:13][C:8]=3[CH:7]=[CH:6][C:5]2=[O:16])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 107521118-cyclopropyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 107057548-cyclopropyl-2-methylsulfinyl-8H-pyrido[2,3-d]pyrimidin-7-oneYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8-cyclopropyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (0.5 g, 2.1 mmol) and 2-benzenesulfonyl-3-phenyl-oxaziridine (0.84 g, 3.2 mmol) in CH2Cl2 (5 mL) was stirred at room temperature for 20 hours. The white solid formed was collected by filtration and washed with hexane, then dried to give 8-cyclopropyl-2-methylsulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (0.388 g, 74%). 1H NMR: δ(400 MHz, DMSO) 9.15 (s, 1H), 8.0 (d, J=9.5 Hz, 1H), 6.74 (d, J=9.5 Hz, 1 H), 2.92(s, 1H), 1.18˜1.14(m, 2H), 0.83˜0.79 (m, 2H).

Workup

  1. customThe white solid formed
  2. filtrationwas collected by filtration
  3. washwashed with hexane
  4. customdried

Sources & evidence

ORD record
ord-75261ae59c7c4ca3b4a31bf0279e1c24
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Reaction notes

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