Triacetoxyperiodinane → Cyclopropyl[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methanone

HRID 410508Notes

Reaction equation

HRID 410508 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH:23]1([CH:26]([C:28]2[S:29][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([NH:39][C:40]4[N:45]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:43]=[CH:42][N:41]=4)[CH:34]=3)=[CH:31][N:32]=2)[OH:27])[CH2:25][CH2:24]1>ClCCl.C(OCC)(=O)C>[CH:23]1([C:26]([C:28]2[S:29][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([NH:39][C:40]4[N:45]=[C:44]([C:46]([F:47])([F:48])[F:49])[CH:43]=[CH:42][N:41]=4)[CH:34]=3)=[CH:31][N:32]=2)=[O:27])[CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67257174Cyclopropyl[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methanol

Product 1

HCID 58456406Cyclopropyl[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methanoneYield 50.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dess-Martin periodinane (110 mg, 0.260 mmol) was added to a stirred, cooled (room temperature) mixture of cyclopropyl[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methanol (Example 4A-5, 85 mg, 0.217 mmol) in dichloromethane (0.72 mL) and the mixture was stirred at room temperature for 30 min. The mixture was cooled, diluted with ethyl acetate, washed with aqueous sodium sulfite then brine, dried (MgSO4), filtered, and concentrated. The residue was purified by flash chromatography to give cyclopropyl[5-(3-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]methanone (43 mg, 0.110 mmol, 50.8%) as a colorless solid. APCI: [M+H]+ m/z 391.0. 1H NMR (400 MHz, CDCl3): δ 8.71 (d, J=4.90, 1H), 8.26 (s, 1H), 8.24 (s, 1H), 7.58-7.50 (m, 2H), 7.46 (t, J=7.87, 1H), 7.42-7.38 (m, 1H), 7.13 (d, J=4.91, 1H), 3.28-3.23 (m, 1H), 1.39-1.34 (m, 2H), 1.22-1.17 (m, 2H). rhSYK activity=+++

Workup

  1. temperaturecooled
  2. temperatureThe mixture was cooled
  3. washwashed with aqueous sodium sulfite
  4. dry with materialbrine, dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-1a14a6ec49b6466c84c5c5dd51c94a8b
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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