2-(Benzenesulfonyl)-3-phenyloxaziridine → 4-Furan-2-yl-6-methanesulfinyl-pyrimidin-2-ylamine

HRID 1356072Notes

Reaction equation

HRID 1356072 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([S:12][CH3:13])[N:9]=[C:8]([NH2:14])[N:7]=1.C1(C2[O:23]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>ClCCl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[C:10]([S:12]([CH3:13])=[O:23])[N:9]=[C:8]([NH2:14])[N:7]=1

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 185076524-Furan-2-yl-6-methylsulfanyl-pyrimidin-2-ylamine

Product 1

HCID 185072094-Furan-2-yl-6-methanesulfinyl-pyrimidin-2-ylamineYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 3.00 g (14.5 mmol) 4-furan-2-yl-6-methylsulfanyl-pyrimidin-2-yl-amine in 150 ml dichloromethane was added 7.56 g (29.0 mmol) 3-phenyl-2-(phenylsulfonyl)oxaziridine and stirring continued for 16 hours at room temperature. The resulting crystals were collected by filtration and washed with dichloromethane to afford 2.92 g (90%) 4-furan-2-yl-6-methanesulfinyl-pyrimidin-2-ylamine as a white crystalline solid. EI-MS m/e (%): 223 (M+, 50), 177 (32), 160 (25), 148 (23), 118 (100), 90 (23), 63 (24).

Workup

  1. filtrationThe resulting crystals were collected by filtration
  2. washwashed with dichloromethane

Sources & evidence

ORD record
ord-37a2ad6f0da1461ab32e8edb60a8a52b
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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