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

HRID 272462Notes

Reaction equation

HRID 272462 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-17147564eba1486a87ec0f14d503137a
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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