Triacetoxyperiodinane → HCID 86612499, compound

HRID 2053083Notes

Reaction equation

HRID 2053083 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:8]=[C:7]([C:21]#[N:22])[N:6]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[O:1]=[CH:2][CH2:3][NH:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:18])[F:20])[CH:12]=2)[N:8]=[C:7]([C:21]#[N:22])[N:6]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58878066HCID 58878066, compound

Product 1

HCID 86612499HCID 86612499, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 4-(2-hydroxy-ethylamino)-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile (308 mg) in dichloromethane (5 ml) was added Dess-Martin periodinane (424 mg) and the resulting suspension was stirred at room temperature for 45 mins. Reaction mixture was diluted with dichloromethane (50 ml) and washed with water (3×50 ml), brine (50 ml), dried over MgSO4 and concentrated in vacuo. The residue was filtered through silica gel pad using heptane and ethyl acetate (1:1) as eluant, solvent was removed in vacuo to give 4-(2-oxo-ethylamino)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile as a white solid (206 mg) MS m/z: 307.5 (M+1).

Workup

  1. customReaction mixture
  2. washwashed with water (3×50 ml), brine (50 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. filtrationThe residue was filtered through silica gel pad
  6. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-0980afe884834fd89b46c522229eb47c
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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