2-(Benzenesulfonyl)-3-phenyloxaziridine → 2-Amino-4-chloro-6-methanesulfinyl-pyrimidine-5-carbonitrile

HRID 1356139Notes

Reaction equation

HRID 1356139 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[C:4]([S:11][CH3:12])[N:3]=1.C1(C2[O:21]N2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>ClCCl.CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[C:4]([S:11]([CH3:12])=[O:21])[N:3]=1

Participants

5

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 185072602-Amino-4-chloro-6-methylsulfanyl-pyrimidine-5-carbonitrile

Product 1

HCID 185072772-Amino-4-chloro-6-methanesulfinyl-pyrimidine-5-carbonitrileYield 69.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 2.00 g (9.97 mmol) 2-amino-4-chloro-6-methylsulfanyl-pyrimidine-5-carbonitrile in 6 ml dichloromethane and 20 ml DMF was added 5.21 g (19.9 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 ether/dichloromethane to afford 1.50 g (69%) 2-amino-4-chloro-6-methanesulfinyl-pyrimidine-5-carbonitrile as a white crystalline solid. ES-MS m/e (%): 239 (M+Na+, 45), 234 (M+NH4+, 55), 217 (M+H+, 100).

Workup

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

Sources & evidence

ORD record
ord-f9683dded9624c16a27081db2d32f211
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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