Methanol → HCID 15003636, compound

HRID 373454Notes

Reaction equation

HRID 373454 reaction equation
C[O-].[Na+].CO.[CH2:6]([S:13][C:14]1[N:18]2[C:19](SC)=[N:20][C:21]([F:23])=[CH:22][C:17]2=[N:16][N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(SC1N=C2N(C(SC)=NC(F)=C2)N=1)C1C=CC=CC=1.C(OCC)(=O)/C=C\[C:49](OCC)=[O:50]>C(O)C.C(O)(=O)C>[CH2:6]([S:13][C:14]1[N:18]=[C:17]2[N:16]([C:19]([O:50][CH3:49])=[N:20][C:21]([F:23])=[CH:22]2)[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 5

HCID 887MethanolHCID 5271566Diethyl MaleateHCID 10942334Sodium MethoxideHCID 150036303-Benzylthio-7-fluoro-5-methylthio-1,2,4-triazolo[4,3-c]pyrimidineHCID 198098512-Benzylthio-7-fluoro-5-methylthio-1,2,4-triazolo[1,5-c]pyrimidine

Product 1

HCID 15003636HCID 15003636, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A 25 percent solution of sodium methoxide in methanol (1.9 ml, 0.0085 mol) was added to a solution of 19.9 g (0.065 mol) of 3-benzylthio-7-fluoro-5-methylthio-1,2,4-triazolo[4,3-c]pyrimidine containing a small amount of 2-benzylthio-7-fluoro-5-methylthio-1,2,4-triazolo[1,5-c]pyrimidine and 11.2 g (0.065 mol) of diethyl maleate in 250 ml of ethanol at ambient temperature with stirring and allowed to react for about 1 hour. Acetic acid (4 ml) was then added and the volatiles were removed by evaporation under reduced pressure. The residue was dissolved in methylene chloride and the resulting solution was extracted with water, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure. The residue was triturated with hexane, filtered, and dried to obtain 10.7 g of the title compound as a white powder melting at 121°-122° C. The nmr and uv spectra were consistent with the assigned structure.

Workup

  1. customto react for about 1 hour
  2. customthe volatiles were removed by evaporation under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. extractionthe resulting solution was extracted with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue was triturated with hexane
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-7a6e954f279e44d4b9354a070500921b
Source dataset
uspto-grants-1992_11
Patent number
US05163995

Reaction notes

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