8-Chlorothieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine → HCID 178509328, compound
Reaction equation
[Cl:1][C:2]1[S:10][C:9]2[N:8]=C[N:6]3[CH:11]=[N:12][N:13]=[C:5]3[C:4]=2[CH:3]=1>CO.C(Cl)Cl>[Cl:1][C:2]1[S:10][C:9]([NH2:8])=[C:4]([C:5]2[NH:6][CH:11]=[N:12][N:13]=2)[CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a stirring mixture of 8-chlorothieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine (60 mg, 0.285 mmol) in MeOH (10 mL) was added N-methylethyl 1,2-diamine (106 mg, 1.4 mmol). The resulting mixture was warmed to 60° C. for 1 hr. The reaction mixture was cooled to rt and then diluted with DCM. This mixture was then washed several times with a saturated NH4Cl solution. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to give 5-chloro-3-(4H-1,2,4-triazol-3-yl)thiophen-2-amine. This amine was taken directly to the next coupling reaction without further purification. Retention time (min)=1.227, method [1], MS (ESI) 201.1 (M+H).
Workup
- temperatureThe reaction mixture was cooled to rt
- washThis mixture was then washed several times with a saturated NH4Cl solution
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b601b6b4440c452a9f273182f0adf02a
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450363B2
Reaction notes
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