88% |
Stage #1: dichloro(1,5-cyclooctadiene)palladium(II); N-(diphenylphosphino)-4-(pyridin-2-yl)pyrimidin-2-amine In dimethyl sulfoxide at 100℃; for 1h;
Stage #2: (tetrahydrothiophene)gold(I) chloride In dimethyl sulfoxide at 100℃; for 0.25h; |
4.5 [(Hpypya)PdCl][AuCl2] (5)
143mg (0.50mmol) of dichloro(1,5-cyclooctadiene)palladium(II) were dissolved in 5ml of DMSO. 178mg (0.50mmol) of N-(diphenylphosphino)-4-(pyridin-2-yl)pyrimidin-2-amine were added under stirring. The yellow mixture was heated to 100°C and stirred for 1h. After cooling down to ambient temperature 160mg (0.50mmol) of chloro(tetrahydrothiophene)gold(I) were added. The yellow solution was heated to 100°C and stirred for 15min. After cooling down to ambient temperature the solution was evaporated. The remaining residue was subsequently dried in vacuo. The product was obtained as a yellow powder. Yield: 337mg (88%). Anal. Calcd C21H17AuCl3N4PPd·C2H6OS, C 32.72, H 2.75, N 6.64, S 3.80, found C, 32.30, H 3.01, N 6.05, S 3.96.1H NMR (300.13MHz, CDCl3): δ (ppm)=9.04 (s, br, 1H, NH), 8.25-8.10 (m, 4H, Ph), 7.98-7.73 (m, 3H, pyridine-3-H, pyridine-5-H, pyridine-6-H), 7.71-7.37 (m, 9H, Ph, pyridine-4-H, pyrimidine-5-H, pyrimidine-6-H).31P{1H} NMR (121.48MHz, CDCl3): δ (ppm)=71.2.IR (ATR): ν (cm-1)=3048 (w), 2963 (w), 1733 (w), 1645 (w), 1591 (m), 1550 (m), 1505 (s), 1464 (m), 1435 (m), 1419 (m), 1331 (m), 1297 (w), 1260 (m), 1216 (m), 1194 (m), 1142 (w), 1103 (s), 1009 (vs), 951 (s), 840 (m), 786 (s), 769 (m), 754 (m), 706 (m), 692 (vs), 636 (m), 536 (vs), 509 (m).Raman (solid state): ν (cm-1)=3057 (w), 2911 (w), 1587 (s), 1477 (m), 1329 (w), 1105 (w), 1037 (w), 1026 (w), 998 (m), 346 (w), 276 (s).ESI-MS (DCM): m/z=499.00 ([(Hpypya)(PdCl)]+). |