Triethylamine → HCID 19097286, compound

HRID 486008Notes

Reaction equation

HRID 486008 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:17]=[C:9]2[N:10]=[C:11](I)[N:12]=[C:13]([S:14][CH3:15])[N:8]2[N:7]=1.[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>CN(C)C=O.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:17]=[C:9]2[N:10]=[C:11]([C:25]#[C:24][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:12]=[C:13]([S:14][CH3:15])[N:8]2[N:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 19097274HCID 19097274, compound

Product 1

HCID 19097286HCID 19097286, compound

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-furyl)-5-iodo-7-methylthio-[1,2,4]triazolo[1,5-a][1,3,5]triazine (2.5 g) and phenyl acetylene (1.5 ml) in dimethylformamide (40 ml) was added triethylamine (1.1 ml), bis(triphenylphosphine)-palladium (II) chloride (0.2 g) and cuprous iodide (0.1 g) and the mixture stirred at room- temperature for 3 hours. The reaction mixture was diluted with water (350 ml) and extracted with ethyl acetate (3×50 ml). The organic extract was washed with water, dried magnesium sulphate and evaporated. The crude product was purified by chromatography on silica-gel (150 g), eluting with ethyl acetate dichloromethane (1% v/v). The residue from the fractions containing the product were triturated with ether and filtered to give 2-(2-furyl)-7-methylthio-5-phenylethynyl-[1,2,4]-triazolo[1,5-a][1,3,5]triazine (1.0 g). Crystallisation of an aliquot from isopropanol gave a yellow crystalline product m.p. 188°-190° C.; microanalysis, found: C, 60.8; H, 3.1; N, 20.9%, C17H11N5OS requires C, 61.2; H, 3.3; N,21.0%; NMR 2.8 (S, 3H, CH3S); 6.75 (d of d, 1H, furyl-4H); 7.35 (d, 1H, furyl-3H), 7.55 (complex, 3H, phenyl-3H, phenyl-4H and phenyl-5H), 7.74 (complex, 2H, phenyl-2H and phenyl-6H) and 8.0 (d, 1H, furyl-5H); m/e 353M+.

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. extractionThe organic extract
  3. washwas washed with water, dried magnesium sulphate
  4. customevaporated
  5. customThe crude product was purified by chromatography on silica-gel (150 g)
  6. washeluting with ethyl acetate dichloromethane (1% v/v)
  7. additionThe residue from the fractions containing the product
  8. customwere triturated with ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-5d7c260871dd43499ef2c9226f60e7e0
Source dataset
uspto-grants-1994_03
Patent number
US05290776

Reaction notes

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