Triacetoxyperiodinane → 4-(3-Methylsulfamoyl-5-tri-fluoromethyl-phenyl)-6-(3-oxo-propyl)-pyrimidine-2-carbonitrile

HRID 733191Notes

Reaction equation

HRID 733191 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([S:21](=[O:25])(=[O:24])[NH:22][CH3:23])[CH:12]=2)[N:8]=[C:7]([C:26]#[N:27])[N:6]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:23][NH:22][S:21]([C:13]1[CH:12]=[C:11]([C:9]2[CH:10]=[C:5]([CH2:4][CH2:3][CH:2]=[O:1])[N:6]=[C:7]([C:26]#[N:27])[N:8]=2)[CH:16]=[C:15]([C:17]([F:19])([F:18])[F:20])[CH:14]=1)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 578391264-(3-Hydroxy-propyl)-6-(3-methylsulphamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile

Product 1

HCID 578391294-(3-Methylsulfamoyl-5-tri-fluoromethyl-phenyl)-6-(3-oxo-propyl)-pyrimidine-2-carbonitrileYield 128.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-(3-hydroxy-propyl)-6-(3-methylsulfamoyl-5-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile (235 mg) and Dess Martin reagent (299 mg) in dichloromethane (5 mL) was stirred at room temperature for 2 h. The reaction mixture was purified by flash silica chromatography to afford 4-(3-methylsulfamoyl-5-tri-fluoromethyl-phenyl)-6-(3-oxo-propyl)-pyrimidine-2-carbonitrile as a pink oil (300 mg). MS m/z 399.0 (M+1), 100%.

Workup

  1. customThe reaction mixture was purified by flash silica chromatography

Sources & evidence

ORD record
ord-48d06b38c4f04a6face725bd3b78e9d0
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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