p-Toluenesulfonic acid → 4-chloro-7-(2,4-dimethoxybenzyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one
반응식
[Cl:1][C:2]1[C:7]([CH2:8][C:9](OC)=[O:10])=[C:6]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[O:23][CH3:24])[N:5]=[CH:4][N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]2[CH2:8][C:9](=[O:10])[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=3[O:23][CH3:24])[C:6]=2[N:5]=[CH:4][N:3]=1참가 물질
4
반응 조건
- 온도
- 10 °C
실험 절차
Combine a solution of methyl 2-(4-chloro-6-(2,4-dimethoxybenzylamino)pyrimidin-5-yl)acetate (1.00 equiv; 2.23 mol; 783 g) in p-toluenesulfonic acid (0.5 equiv; 1.10 mol; 212 g) with Toluene (12 L) and stir at reflux. After 1 h, remove toluene in vacuo and extract with DCM. Wash the organic layer with saturated NaHCO3(aq) and brine, dry over Na2SO4, filter and concentrated in vacuo. Slurry the residue in methanol (2 L) and concentrate in vacuo to approximately 1 L. Cool the slurry to 10° C., filter, wash with cold methanol, and dry to obtain the title compound (1.65 mol; 527 g; 74.05%) as a yellow-orange solid. 1H NMR (400 MHz, CDCl3): 8.59 (s, 1H), 7.13 (d, J=8.4 Hz, 1H), 6.43 (d, J=2.0 Hz, 1H), 6.40 (d, J=8.5 Hz, 1H), 4.92 (d, s, 2H), 3.79 (s, 3H), 3.77 (s, 3H), 3.60 (s, 2H).