2-(Benzenesulfonyl)-3-phenyloxaziridine → 5-Bromo-4-furan-2-yl-6-methanesulfinyl-pyrimidin-2-ylamine

HRID 1355847Notes

Reaction equation

HRID 1355847 reaction equation
[Br:1][C:2]1[C:3]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[N:4][C:5]([NH2:10])=[N:6][C:7]=1[S:8][CH3:9].C1(C2[O:24]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>ClCCl>[Br:1][C:2]1[C:3]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[N:4][C:5]([NH2:10])=[N:6][C:7]=1[S:8]([CH3:9])=[O:24]

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 185075225-Bromo-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine

Product 1

HCID 185072865-Bromo-4-furan-2-yl-6-methanesulfinyl-pyrimidin-2-ylamineYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 350 mg (1.22 mmol) 5-bromo-4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine in 30 ml dichloromethane was added 1.28 g (4.89 mmol) 3-phenyl-2-(phenylsulfonyl)oxaziridine and stirring continued for 16 hours at room temperature. The reaction mixture was then concentrated in vacuo and the residue recrystallised from hexane/dichloromethane to afford 225 mg (61%) 5-bromo-4-furan-2-yl-6-methanesulfinyl-pyrimidin-2-ylamine as a beige crystalline solid. EI-MS m/e (%): 303 (M{flBr}+, 24), 301 (M{79Br}+24), 257(48), 255 (50), 198 (81), 196(84), 117(100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue recrystallised from hexane/dichloromethane

Sources & evidence

ORD record
ord-cd06cf46cefa459c9cb93cc60644bb99
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

Loading…