Phenol → HCID 59639611, compound

HRID 2249781Notes

Reaction equation

HRID 2249781 reaction equation
Cl[C:2]1[C:7]([CH:8]=[O:9])=[C:6]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[N:5]=[C:4]([S:18][CH3:19])[N:3]=1.[H-].[Na+].[C:22]1([OH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CS(C)=O>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[NH:10][C:6]1[C:7]([CH:8]=[O:9])=[C:2]([O:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:3]=[C:4]([S:18][CH3:19])[N:5]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 9944656HCID 9944656, compound

Product 1

HCID 59639611HCID 59639611, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-chloro-6-(2-chloro-phenylamino)-2-methylsulfanyl-pyrimidine-5-carbaldehyde (315 mg, 1 mmol) in 10 mL of anhyd DMSO was added NaH (50 mg, 1.2 mmol, 60% dispersion in mineral oil, 1.2 eq) followed by phenol (112 mg, 1.2 mmol, 1.2 eq). The reaction mixture was stirred for 1 h 23°, quenched with H2O (20 mL), Et2O (100 mL) was added and the layers were separated. The organic layer was washed with satd aq NaCl, dried (MgSO4) filtered and solvent was removed in vacuo. The yellow residue was then purified by Flash chromatography to afford 120 mg (45% yield) of 4-(2-chloro-phenylamino)-2-methylsulfanyl-6-phenoxy-pyrimidine-5-carbaldehyde. 1H-NMR δ 2.32 (s, 3H), 7.01-7.49 (m, 8H), 8.51 (d, 1H, J=7.2 Hz), 10.49 (s, 1H), 11.58 (br s, 1H). LC MS (m/e)=372 (MH+). Rt=2.94 min.

Workup

  1. customquenched with H2O (20 mL), Et2O (100 mL)
  2. additionwas added
  3. customthe layers were separated
  4. washThe organic layer was washed with satd aq NaCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customsolvent was removed in vacuo
  8. customThe yellow residue was then purified by Flash chromatography

Sources & evidence

ORD record
ord-fa08768346384c298584160ea494a2c5
Source dataset
uspto-grants-2008_01
Patent number
US07314881B2

Reaction notes

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