Methyl iodide → HCID 19097285, compound

HRID 486011Notes

Reaction equation

HRID 486011 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:9]2[N:10]=[C:11]([C:13]3[O:14][CH:15]=[CH:16][CH:17]=3)[N:12]=[C:8]2[N:7]=[C:6]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)[N:5]=1.IC.[CH3:28]C(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>CN(C)C=O.O>[F:25][C:20]1[CH:19]=[C:18]([C:6]2[N:5]=[C:4]([NH:3][CH3:28])[N:9]3[N:10]=[C:11]([C:13]4[O:14][CH:15]=[CH:16][CH:17]=4)[N:12]=[C:8]3[N:7]=2)[CH:23]=[C:22]([F:24])[CH:21]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 19097282HCID 19097282, compound

Product 1

HCID 19097285HCID 19097285, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (86 mg of a 50% dispersion in oil) was added to a stirred solution of 7-amino-5-[3,5-difluorophenyl]-2-(2-furyl)-1,2,4-triazolo[1,5-a][1,3,5]triazine (0.421 g) in dimethylformamide (5 ml). The mixture was stirred until the effervesence had ceased and a clear solution was obtained. Iodomethane (0.256 g, 0.11 ml) was then added and the reaction mixture was stirred at ambient temperature for 2 hours. Water (25 ml) and glacial acetic (0.5 ml) were then added and the resulting aqueous suspension was extracted with ethyl acetate (3×50 ml). The organic extracts were combined and washed with water (2×25 ml) and brine (25 ml), dried (MgSO4) and evaporated to give a yellow solid. This was purified by chromatography on silica. Elution with toluene containing ethyl acetate (10% v/v) gave 5-[3,5-difluorophenyl]-2-(2-furyl)-7-methylamino-[1,2,4]triazolo[1,5-a][1,3,5]triazine as a white solid m.p. 231°-4° C. microanalysis, found: C, 55.0; H, 3.1; N, 25.5% C15H10F2N6O requires C15H10F2N6O C, 54.9; H, 3.1; N, 25.6%; NMR 3.16 (s, 3H, CH3N), 6.73 (d of d, 1H, furyl-4H), 7.21 (d of d, 1H, furyl-3H), 7.47 (t of t, 1H, phenyl-4H), 7.93 (d, 1H, furyl-5H), 7.97-8.05 (complex, 2H, phenyl-2H and phenyl-6H) and 9.31 (s, 1H, NH); m/e 329 (M+H)+.

Workup

  1. customa clear solution was obtained
  2. stirringthe reaction mixture was stirred at ambient temperature for 2 hours
  3. extractionthe resulting aqueous suspension was extracted with ethyl acetate (3×50 ml)
  4. washwashed with water (2×25 ml) and brine (25 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a yellow solid
  8. customThis was purified by chromatography on silica
  9. washElution with toluene
  10. additioncontaining ethyl acetate (10% v/v)

Sources & evidence

ORD record
ord-26f685c50891488d988b7822ab747d24
Source dataset
uspto-grants-1994_03
Patent number
US05290776

Reaction notes

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