I. Đurić thinks that he could be the same person as the priest Dobro, who was sent along with the Sebast Grapsa by the Serbian King Stefan Uroš II Milutin as an envoy to Charles II, the King of Naples in March 1302 (ut virum nobilem Sebasto Grapsam et presbiterum Dobronem, nuncios Excellentis principi domini Urosii). Mentioned in the sermon of the Byzantine writer Theodoros Metochites, who undertook the task to arrange the marriage of the Byzantine princess Simonis with the Serbian King Stefan Uroš II Milutin. He held the position of an Ekklesiarches. Janković believes that Tomprailos was in the service of the Archbishopric of Skopje. He accompanied Dukaites along with the monk Damianos around 1298 at the request of the Serbian King Stefan Uroš Milutin to Constantinople (κἀγὼ μὲν αὐτίκα τὸν καλὸν Δουκαίτην ἐς βασιλέα· καὶ αὐτὸς δὲ οὕστινας οἶσθα, σὺν αὐτῷ πέμπομεν, Δαμιανόν τινα αὐτὸν οἶμαι ὄνομα μοναχὸν καὶ Τομπράιλον ἐκκλησιάρχην ἐνταῦθα τοῖς ἐγχωρίοις τετιμημένον τοῦ δεσπότου καὶ κατωνομασμένον· περί τε τοῦ παντὸς ἔργου κατεροῦντας ὡς ἤνυσταί τε καὶ πεπέρανται· καὶ καταλιπαρήσοντας ἐξ αὐτοῦ δεσπότου τὲ καὶ Τριβαλλάρχου, καὶ ἤδη παιδὸς φίλου τῷ βασιλεῖ, περὶ οὗ νῦν γε εἴρηται συνθήματος).