Sodium hydride → HCID 21865074, compound

HRID 858983Notes

Reaction equation

HRID 858983 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][C:19]1[S:20][C:21]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][C:22]=2[N:23]=1.[H-].[Na+]>CN(C=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[CH:13][N:14]=[C:15]([O:28][C:25]3[CH:26]=[CH:27][C:21]4[S:20][C:19]([CH3:18])=[N:23][C:22]=4[CH:24]=3)[CH:16]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6997992-Methyl-1,3-benzothiazol-5-olHCID 16749212HCID 16749212, compound

Product 1

HCID 21865074HCID 21865074, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 100-mL, round-bottomed flask containing 4-(4-tert-butyl-phenyl)-6-chloro-pyrimidine, (Example 1(a)), (0.15 g, 0.61 mmol) and 2-methyl-benzothiazol-5-ol (0.14 g, 0.85 mmol, Aldrich) in DMF (10 mL), was added NaH (34 mg, 0.85 mmol, 60% in mineral oil, Aldrich) at room temperature. The solution was then stirred at room temperature for 4 h. After the solvent was removed in vacuum, EtOAc (10 mL) was added to the residue, and the organic layer was washed with water (8 mL), dried over Na2SO4, filtered, and concentrated in vacuum. After purifying the crude product by silica gel chromatography (4:1 hexanes/EtOAc), the resulting solid was dissolved in acetone (5 mL). Water (8 mL) was added dropwise to this mixture, and a white precipitate fell out of solution, which was collected by filtration, washed with water (0.5 mL), and dried under vacuum at 50° C. for 48 h to furnish the title compound. Mp: 163–165° C. MS (ESI, pos. ion) m/z: 376 (M+1). Anal. Calcd for C23H21N3OS.(H2O)1/3: C, 69.26; H, 5.72; N, 11.01. Found: C, 69.19; H, 5.61; N, 11.03.

Workup

  1. customAfter the solvent was removed in vacuum, EtOAc (10 mL)
  2. additionwas added to the residue
  3. washthe organic layer was washed with water (8 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customAfter purifying the crude product by silica gel chromatography (4:1 hexanes/EtOAc)
  8. dissolutionthe resulting solid was dissolved in acetone (5 mL)
  9. additionWater (8 mL) was added dropwise to this mixture
  10. filtrationwas collected by filtration
  11. washwashed with water (0.5 mL)
  12. customdried under vacuum at 50° C. for 48 h

Sources & evidence

ORD record
ord-cb7891c8aa4140d88f46b1a17ab0a0ee
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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