Aug. 2, 2007  26  US 2007/0179263 A 1  Example 1  Synthesis of  perfluoro(2,5-bistrifluoromethyl-3,6-dioxanonanoic  acid)-(2-pyrimidine )amide  Example 3  Synthesis of perfluoro(2,5,8-tristrifluoromethyl-3,6,  9-trioxadodecanoic acid)-(2-pyrimidine )amide  Example 2  Synthesis of N-perfluoro(l, l-dihydro-2,5-bistrifluo› romethy 1-3, 6-dioxanonanoy I) -N-(2-pyrimidine)  Into a 500 ml four-necked flask equipped with a  thermometer and dropping funnel were poured 150  ml of sulfolane, 60 g of perfluoro(l,1-dihydro-2,5- bistrifluoromethy 1-3, 6-dioxanonanoy 1)-ortho-ni- tro benzenesulfonate:  [0221]  Into a 500 ml four-necked flask equipped with a  thermometer and dropping funnel were poured 150 ml of  dehydrated DMF, 57 g of aminopyrimidine and 42 g of  triethylamine in a nitrogen atmosphere. On an ice bath, 176  g  of perfluoro(2,5-bistrifluoromethyl-3,6-dioxanonanoic  acid chloride:  was slowly added dropwise with stirring. After completion  of the addition, the mixture temperature was increased to  room temperature gradually and stirring was carried out at  room temperature for one hour. The reaction solution was  subjected to separation with an acid and water to take out an  oil layer. After drying of the oil layer with magnesium  sulfate, distillation was carried out under reduced pressure  and 142 g of perfluoro(2,5-bistrifluoromethyl-3,6-diox› anonanoic acid)-(2-pyrimidine )amide:  was obtained. According to $^{19}$F-NMR and $^{1}$H-NMR analy› ses, it was confirmed that the obtained product was the  above-mentioned compound. This compound was soluble in  acetone and ethyl acetate and was in the form of liquid at  room temperature. Also as a result of TGA measurement in  the air, Tdlo was 159°  C. and Tdso was 188°  C.  [0222]  $^{19}$F-NMR (CD$_{3}$COCD$_{3}$ ): -78 to -80 ppm (7F),  -82 to -85 ppm (4F), -92 ppm (2F), -115 ppm (2F), -132  ppm (IF), -145.0 ppm (IF) $^{1}$H-NMR (CD3COCD3): 7.2  ppm (lH), 8.7 ppm (2H), 9.0 ppm (lH)  [0223]  and 34 g of aminopyrimidine in a nitrogen atmosphere,  followed by stirring at 170°  C. for 24 hours in a nitrogen  atmosphere. The reaction solution was poured into water,  and a solid was removed by filtration. The filtrate was  subjected to separation with water/ethyl acetate to take out  an oil layer. After drying of the oil layer with magnesium  sulfate, distillation was carried out under reduced pressure  and 17 g of N-perfluoro(l, l-dihydro-2,5-bistrifluoromethyl- 3,6-dioxanonanoyl)-N-(2-pyrimidine ):  was obtained. According to $^{19}$F-NMR and $^{1}$H-NMR analy› ses, it was confirmed that the obtained product was the  above-mentioned compound. This compound was soluble in  acetone and ethyl acetate and was in the form of liquid at  room temperature. Also as a result of TGA measurement in  the air, Td$_{10 }$was 122°  C. and Tdso was 138°  C.  [0224]  $^{19}$F-NMR (CD$_{3}$COCD$_{3}$ ): -78 to -80 ppm (7F),  -82 to -85 ppm (4F), -94 ppm (2F), -112 ppm (2F), -143  ppm (IF), -168 ppm (IF) $^{1}$H-NMR (CD$_{3}$COCD$_{3}$): 2.8 ppm  (lH), 3.6 ppm (2H), 7.2 ppm (lH), 8.7 ppm (2H), 9.0 ppm  (lH)  [0225]  Into a 500 ml four-necked flask equipped with a  thermometer and dropping funnel were poured 150 ml of  dehydrated DMF, 50 g of aminopyrimidine and 42 g of  triethylamine in a nitrogen atmosphere. On an ice bath, 160  g  of perfluoro(2,5,8-tristrifluoromethyl-3,6,9-trioxadode› canoic acid chloride):  was slowly added dropwise with stirring. After completion  of the addition, the mixture temperature was increased to  room temperature gradually and stirring was carried out at  room temperature for one hour. The reaction solution was  subjected to separation with an acid and water to take out an  oil layer. After concentration of the oil layer, 136 g of  perfluoro(2,5,8-tristrifluoromethyl-3,6,9-trioxadodecanoic  acid)-(2-pyrimidine )amide:  was obtained. According to $^{19}$F-NMR and $^{1}$H-NMR analy› ses, it was confirmed that the obtained product was the  above-mentioned compound. This compound was soluble in  acetone and ethyl acetate and was in the form of liquid at  room temperature. Also as a result of TGA measurement in  the air, Td$_{10 }$was 180°  C. and Tdso was 209°  C. 