Sodium hydride → 7-{1-[4-(Ethylthio)phenoxy]ethyl}-1,2,4-triazolo[1,5-a]pyrimidine

HRID 1290808Notes

Reaction equation

HRID 1290808 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:2].[H-].[Na+].Br[CH:14]([C:16]1[N:21]2[N:22]=[CH:23][N:24]=[C:20]2[N:19]=[CH:18][CH:17]=1)[CH3:15]>COCCOC>[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:14]([C:16]2[N:21]3[N:22]=[CH:23][N:24]=[C:20]3[N:19]=[CH:18][CH:17]=2)[CH3:15])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 130853494-(Ethylthio)phenolHCID 189193517-(1-Bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine

Product 1

HCID 97963597-{1-[4-(Ethylthio)phenoxy]ethyl}-1,2,4-triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 4-(ethylthio)phenol (1.54 g) in dry 1,2-dimethoxyethane was added slowly to a stirred suspension of sodium hydride (0.48 g) in dry 1,2-dimethoxyethane (35 ml). The mixture was stirred for 30 minutes, then a solution of 7-(1-bromoethyl)-1,2,4-triazolo[1,5-a]pyrimidine (2.27 g, prepared in a similar manner to that described in Example 6 above) in dry 1,2-dimethoxyethane (85 ml) was added dropwise. The reaction mixture was stirred overnight at room temperature. The sodium bromide was removed from the mixture by filtration. The solvent was evaporated from the mixture and the residue dissolved in dichloromethane and washed with 200 ml of a 5% aqueous solution of sodium hydroxide followed by water. The organic layer was dried over magnesium sulphate. Evaporation of the solvent afforded a crude product which was purified by column chromatography on silica gel using as eluent a mixture of diethylether and ethyl acetate (in the ratio 6:4 respectively), followed by recrystallisation from a mixture of ethyl acetate and hexane, to give 7-{1-[4-(ethylthio)phenoxy]ethyl}-1,2,4-triazolo[1,5-a]pyrimidine. Yield 2.28 g, (m.p. 65°-67° C.).

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. customThe sodium bromide was removed from the mixture by filtration
  4. customThe solvent was evaporated from the mixture
  5. dissolutionthe residue dissolved in dichloromethane
  6. washwashed with 200 ml of a 5% aqueous solution of sodium hydroxide
  7. dry with materialThe organic layer was dried over magnesium sulphate
  8. customEvaporation of the solvent
  9. customafforded a crude product which
  10. customwas purified by column chromatography on silica gel using as eluent
  11. additiona mixture of diethylether and ethyl acetate (in the ratio 6:4 respectively),
  12. customfollowed by recrystallisation from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-c5d39e04784c4739ba9e3899325066ab
Source dataset
uspto-grants-1998_05
Patent number
US05753665

Reaction notes

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