Table 1.

Reagents and conditions in the synthesis of compounds 2a, 2b, 3, D-Cl and D-N<P>NH.

Entry	Reaction	Conditionsa
1	1 → 2a, 2b	(i) 1.00 equiv n-C8H17-I, 8.00 equiv K2CO3, acetone, −13 °C, 3 h; rt, 12 h; (ii) 1.00 equiv n-C8H17-I, rt, 72 h; 50 °C, 8 h/N2
2	4-OOA → 2ab	(i) 0.50 equiv C3N3Cl3, acetone, 0–5 °C, 2 h; (ii) 1.00 equiv NaHCO3, H2O, 0–5 °C; 45 °C, 3 h; rt, 18 h/N2
3	2a → 3	4.00 equiv piperazine, 1.00 equiv K2CO3, THF, rt, 34 h
4	3 → D-Cl	0.50 equiv C3N3Cl3, 1.00 equiv K2CO3, THF, −10 °C, 3 h; rt, 36 h; reflux, 24 h
5	D-Cl → D-N<P>NH	4.00 equiv piperazine, 1.00 equiv K2CO3, THF, rt, 40 h; reflux, 15 h

^aFor comments about these conditions, see section 3.1. ^bThe same double amination of cyanuric chloride with 4-(n-octyloxy)aniline was reported by S. Yagai and co-workers in 2012 [23], with no isolation of 2a, as it was submitted in situ to ammonolysis to give 2-amino-4,6-bis[4-(n-octyloxy)phenylamino]-s-triazine (75% overall yield).