Ethanol → 8-(4-Fluorophenyl)-5-methylthio-7-(4-pyridyl)-1,2,4-triazolo[4,3-c]pyrimidine

HRID 897393Notes

Reaction equation

HRID 897393 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[C:6]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[N:5]=[C:4]([S:21][CH3:22])[N:3]=1.[NH2:23][NH2:24].O.[CH3:26]CO>>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[C:2]3[N:3]([CH:26]=[N:23][N:24]=3)[C:4]([S:21][CH3:22])=[N:5][C:6]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 223466344-Chloro-5-(4-fluorophenyl)-2-methylthio-6-(4-pyridyl)pyrimidine

Product 1

HCID 223466278-(4-Fluorophenyl)-5-methylthio-7-(4-pyridyl)-1,2,4-triazolo[4,3-c]pyrimidine

Procedure

A solution of 0.28 g of 4-chloro-5-(4-fluoro phenyl)-2-methylthio-6-(4-pyridyl)pyrimidine (0.85 mmol) and 3 ml of NH2NH2—H2O in 20 ml EtOH in a 50-ml r.b.flask with a stir bar was stirred at 70° C. The solvents were evaporated and the residue was mixed with toluene. The residue was dried by removal water with toluene and further dried under vacuum at 50° C. overnight. The resulting light yellow solid was mixed with 40 ml of DCM, 4 ml of CH(OCH3)3, and 2 ml of TFA in a 100-ml r.b.flask with a stir bar. The reaction solution was stirred at RT overnight. The acidic reaction solution was neutralized to pH 8 with sat'd NaHCO3. The DCM layer was washed with brine (10 ml) and dried over Na2SO4. After removal of the DCM in vacuo, 8-(4-fluorophenyl)-5-methylthio-7-(4-pyridyl)-1,2,4-triazolo[4,3-c]pyrimidine was obtained as yellow solid; MS m/z (M+H)+ 338.1; C17H12FN5S requir. 337.3.

Workup

  1. customThe solvents were evaporated
  2. additionthe residue was mixed with toluene
  3. dry with materialThe residue was dried by removal water with toluene
  4. customfurther dried under vacuum at 50° C. overnight
  5. additionThe resulting light yellow solid was mixed with 40 ml of DCM, 4 ml of CH(OCH3)3, and 2 ml of TFA in a 100-ml r.b.flask with a stir bar
  6. washThe DCM layer was washed with brine (10 ml)
  7. dry with materialdried over Na2SO4
  8. customAfter removal of the DCM in vacuo

Sources & evidence

ORD record
ord-c7d9acbfa0a344dc93a247dce98b2739
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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