[N:1]1[N:2]=[CH:3][N:4]2[C:9]=1[C:8]1[CH:10]=[CH:11][S:12][C:7]=1[N:6]=[CH:5]2.C1C(=O)N([Cl:20])C(=O)C1.C([O-])(O)=O.[Na+]>CC(O)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:20][C:11]1[S:12][C:7]2[N:6]=[CH:5][N:4]3[CH:3]=[N:2][N:1]=[C:9]3[C:8]=2[CH:10]=1To a stirring mixture of thieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine (123 mg, 0.7 mmol) in HOAc (1 mL) was added NCS (200 mg, 1.5 mmol), Pd(OAc)2 (48 mg, 0.21 mmol). The reaction mixture was stirred at 120° C. overnight. The reaction was neutralized with a saturated NaHCO3 solution and extracted with DCM. This product was purified via an isco column to give 8-chlorothieno[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine as the major product. Retention time (min)=1.663, method [1], MS(ESI) 211.0 (M+H).
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