Triacetoxyperiodinane → 1-(2-((3-Bromo-5-methylphenyl)amino)pyrimidin-4-yl)ethanone

HRID 595165Notes

Reaction equation

HRID 595165 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([CH:16]([OH:18])[CH3:17])[CH:13]=[CH:12][N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([C:16](=[O:18])[CH3:17])[CH:13]=[CH:12][N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 1182087631-(2-((3-Bromo-5-methylphenyl)amino)pyrimidin-4-yl)ethanol

Product 1

HCID 1182087071-(2-((3-Bromo-5-methylphenyl)amino)pyrimidin-4-yl)ethanone

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-(2-((3-Bromo-5-methylphenyl)amino)pyrimidin-4-yl)ethanol (3.27 g, 10.59 mmol) was dissolved in dichloromethane (14 mL). Dess-Martin Periodinane (9.0 g, 21.2 mmol) was added, and the resultant suspension was stirred vigorously for 14 h at room temperature. The mixture was diluted with saturated aqueous sodium bicarbonate and sodium thiosulfate. The heterogeneous mixture was extracted with dichloromethane (2×). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica (10-40% ethyl acetate/hexanes) to afford 1-(2-((3-bromo-5-methylphenyl)amino)pyrimidin-4-yl)ethanone as a yellow solid. MS ESI calc'd. for C13H13BrN3O [M+H]+ 306, 308. found 306, 308. 1H NMR (500 MHz, CDCl3) δ 8.64 (d, J=4.9 Hz, 1H), 7.93 (s, 1H), 7.35-7.30 (m, 2H), 7.05 (s, 1H), 2.71 (s, 3H), 2.35 (s, 3H).

Workup

  1. extractionThe heterogeneous mixture was extracted with dichloromethane (2×)
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica (10-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2a82cbd13c1945e78a776cc193979f48
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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