Sodium hydride → HCID 11462750, compound

HRID 1383829Notes

Reaction equation

HRID 1383829 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[N:4]=1.[H-].[Na+].Cl[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]2=[N:23][N:24]=[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:15]2[N:14]=1>CN(C)C=O>[CH3:9][C:5]1[N:4]=[C:3]([CH2:2][O:1][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]3=[N:23][N:24]=[C:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:15]3[N:14]=2)[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 707366-Methyl-2-pyridylmethanolHCID 15025636-chloro-3-phenyl-[1,2,4]triazolo[3,4-a]phthalazine

Product 1

HCID 11462750HCID 11462750, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-hydroxymethyl-6-methylpyridine (Example 67 part b, 0.5 g), in anhydrous dimethylformamide (20 ml) under nitrogen was added sodium hydride (107 mg of 60% in oil) and the reaction mixture was stirred at room temperature for 0.5 hours. To this mixture was added 6-chloro-3-phenyl-1,2,4-triazolo[3,4-a]phthalazine (Example 67 part d, 330 mg) and the solution was heated to 80° C. for 0.25 hours. After cooling the solvent was removed under vacuum, and the residue was dissolved in dichloromethane (30 ml) and washed with water and brine. After drying (MgSO4), the solution was filtered and evaporated to give the required product which was recrystallised from a mixture of ethyl acetate and hexane to give the title compound (210 mg, m.p. 186-187° C.). 1H NMR (360 MHz, DMSO) δ 2.52 (3H, s), 5.65 (2H, s), 7.25 (1H, d, J=7.7Hz), 7.49 (1H, d, J=7.7Hz), 7.58 (3H, m), 7.76 (1H, t, J=7.7Hz), 7.94 (1H, t, J=7.6Hz), 8.08 (1H, t, J=7.7Hz), 8.30 (3H, m), 8.58 (1H, d, J=7.6Hz); MS (ES+) m/e 368 [MH]+. Anal. Found C, 71.32; H, 4.44; N. 18.53. C22H17N5O. H2O requires C, 71.22; H, 4.73; N, 18.88%.

Workup

  1. temperaturethe solution was heated to 80° C. for 0.25 hours
  2. temperatureAfter cooling the solvent
  3. customwas removed under vacuum
  4. dissolutionthe residue was dissolved in dichloromethane (30 ml)
  5. washwashed with water and brine
  6. dry with materialAfter drying (MgSO4)
  7. filtrationthe solution was filtered
  8. customevaporated

Sources & evidence

ORD record
ord-8d231c49cb6c4f8da8a1b7893839a279
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

Loading…