Sodium hydride → HCID 21865296, compound

HRID 857619Notes

Reaction equation

HRID 857619 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[C:25]([CH3:30])[CH:24]=[C:23]2[OH:31].[H-].[Na+]>CN(C=O)C>[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[C:25]([CH3:30])[CH:24]=[C:23]2[O:31][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidineHCID 178487856HCID 178487856, compound

Product 1

HCID 21865296HCID 21865296, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 100-mL, round bottomed flask containing 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (0.26 g, 1.0 mmol) and 6-methoxy-2-methyl-quinolin-4-ol (0.19 g, 1.0 mmol, Ubichem) in DMF (5 mL), was added NaH (48 mg, 1.2 mmol, 60% in mineral oil, Aldrich) at room temperature The solution was then stirred at room temperature for 24 h. After the solvent was removed in vacuum, EtOAc (30 mL) was added to the residue, and the mixture was washed with brine (2×15 mL), dried over Na2SO4, filtered, and concentrated in vacuum. After the product was purified by silica gel chromatography (5:1 hexanes/EtOAc), the resulting solid was dissolved in acetone (10 mL) and MeOH (8 mL). Water (15 mL) was then added dropwise to afford a white precipitate, which was collected by filtration, washed with water (2 mL), and dried under vacuum at 50° C. for 48 h to furnish the title compound. Mp: 165–166° C. MS (ESI, pos. ion) m/z: 412; Anal. Calcd for C22H16F3N3O2: C, 64.23; H, 3.92; N, 10.21. Found: C, 64.20; H, 3.85; N, 10.14.

Workup

  1. customAfter the solvent was removed in vacuum, EtOAc (30 mL)
  2. additionwas added to the residue
  3. washthe mixture was washed with brine (2×15 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customAfter the product was purified by silica gel chromatography (5:1 hexanes/EtOAc)
  8. dissolutionthe resulting solid was dissolved in acetone (10 mL)
  9. additionWater (15 mL) was then added dropwise
  10. customto afford a white precipitate, which
  11. filtrationwas collected by filtration
  12. washwashed with water (2 mL)
  13. customdried under vacuum at 50° C. for 48 h

Sources & evidence

ORD record
ord-2afbf41210d24fac84725f348c7e9818
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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