Table 3.
Characterization of Xanthine Derivatives
| compd | methoda | % yieldb | mp (°C) | MSc | formula | analysis |
|---|---|---|---|---|---|---|
| 4 | A | 75 | 165.5–169 | EI: 164 (M+) | C13H20N4O2 | C, H, N |
| 7 | A | 68 | 137–140 | EI: 298 (M+) | C16H18N4O2 | C, H, N |
| 11 | B | 60 | 170–172 | FAB: 426 (M+ + 1) | C11H14N4O4 | f |
| 12ad | C | 57 | 192–194 | FAB: 454 (M+ + 1) | C23H27N5O5 | C, H, Nf |
| 12b | C | 66e | 159–160 | FAB: 440 (M+ + 1) | C22H25N5O5·0.5DMF | C, H, Nf |
| 14 | B | 32 | 260–263 | 335, 352 | C16H22N4O4·0.5DMF | C, H, N |
| 15 | C | 91 | 129–130 | 363 | C17H24N4O4 | C, H, N |
| 16 | C | 66 | 225–230 | 349 | C17H24N4O4·0.5DMF | C, H, N |
| 17 | B | 45 | 229–230 | 337 (M+ + 1), 354 (M+ + 18) | C16H24N4O4 | C, H, N |
| 18 | B | 39 | 189–191 | 348, 365 | C17H26N4O4 | C, H, N |
| 19 | B | 19 | 225 dec | 365, 382 | C18J28N4O4·0.15NH4OH | C, H, N |
| 20 | B | 56 | 239–240 | 267 (M+ + 1) | C11H14N4O4 | C, H, N |
| 21 | B | 48 | 245–247 dec | 283 (M+ + 1), 300 (M+ + 18) | C11H14N4O3S1·1.18H2O | C, H, N |
| 30 | D | 57 | 325–330 dec | 415 (M+ + 1) | C21H26N4O5·0.5NH4OH | C, H, N |
| 33 | D | 78 | 172–173 | C40H43N7O9·1.5H2O | C, H, N | |
| 34 | D | 100 | 215–220 dec | 544 | C25H33N7O7·1.5H2O | C, H, N |
| 35 | D | 70 | 204–207 dec | FAB: 644 (M+ + 1) | C23H33N8O10 | f |
a
Methods: (A) synthesis as in Scheme 1; (B) synthesis as in Scheme 2; (C) refer to text; (D) refer to Scheme 3.
b
Percent yield calculated from 1,3-dialkyl-6-amino-5-nitrosouracil.
c
CI, unless noted.
d
Methyl ester of compound 12b.
e
Saponification step.
f
High-resolution mass, measured (ppm from calculated), in FAB mode: 11, 426.1778 (+0.1); 12a, 454.2091 (+0.2); 12b, 440.1944 (+2.2); 35, 644.2686 (+0.8).