Ethanol → 5-Methylthio-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

HRID 897401Notes

Reaction equation

HRID 897401 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[C:6]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[CH:19]=2)[N:5]=[C:4]([S:25][CH3:26])[N:3]=1.[NH2:27][NH2:28].O.[CH3:30]CO>>[CH3:26][S:25][C:4]1[N:3]2[CH:30]=[N:27][N:28]=[C:2]2[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[C:6]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([Cl:24])[CH:19]=2)[N:5]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 223466514-Chloro-6-(2-chloro-4-pyridyl)-2-methylthio-5-(3-(trifluoromethyl)-phenyl)pyrimidine

Product 1

HCID 223465775-Methylthio-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

Procedure

4-Chloro-6-(2-chloro-4-pyridyl)-2-methylthio-5-(3-(trifluoromethyl)-phenyl)pyrimidine (0.873 g, 2.1 mmol) and 16.5 ml of NH2NH2—H2O in 90 ml EtOH in a 150-ml r.b.flask with a stir bar was stirred at 70° C. The reaction was cooled to room temperature. The solvents were evaporated in vacuo. The residue was dried by addition and removal of toluene in vacuo and further dried under vacuum at 50° C. overnight. The resulting light yellow solid was mixed with 40 ml of DCM, 20 ml of CH(OCH3)3, and 10 ml of TFA in a 150-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 by sat'd NaHCO3. The DCM layer was washed with brine (3×20 ml) and dried over Na2SO4. After removal of the DCM in vacuo, crude product (MS m/z 421.8 (M+H)+) was obtained as a dark brown oil, which was used directly in the next step.

Workup

  1. customThe solvents were evaporated in vacuo
  2. dry with materialThe residue was dried by addition and removal of toluene in vacuo
  3. customfurther dried under vacuum at 50° C. overnight
  4. additionThe resulting light yellow solid was mixed with 40 ml of DCM, 20 ml of CH(OCH3)3, and 10 ml of TFA in a 150-ml r.b.flask with a stir bar
  5. washThe DCM layer was washed with brine (3×20 ml)
  6. dry with materialdried over Na2SO4
  7. customAfter removal of the DCM in vacuo
  8. customcrude product (MS m/z 421.8 (M+H)+) was obtained as a dark brown oil, which

Sources & evidence

ORD record
ord-da7ca83d74324149892d0cfb0f8813cb
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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