Ammonium Hydroxide → 1,1-dimethylethyl 3-(4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-azetidinecarboxylate
反応式
[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH:12]2[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]2)[CH:3]=1.[OH-].[NH4+:24]>>[NH2:24][C:9]1[C:10]2[C:2]([Br:1])=[CH:3][N:4]([CH:12]3[CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]3)[C:5]=2[N:6]=[CH:7][N:8]=1参加物
3
反応条件
- 温度
- 100 °C
実験手順
To 1,1-dimethylethyl 3-(5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-azetidinecarboxylate (690 mg, 1.780 mmol) was added ammonium hydroxide (69.3 μl, 1.780 mmol) in a 20 mL microwave vial. The vial was capped heated at 100° C. for a total of 2 hr in the microwave reactor. The reaction was checked every 0.5 hr. Only 15% desired product was observed. The reaction was filtered. The solid was added NH4OH (4 mL) into a 20 ml microwave vial and the vial was heated in an oil bath at 90° C. for 24 hr. The reaction observed 80% product. Additional 1 ml of NH4OH was added and heating continued overnight. The reaction was filtered and washed to give 1,1-dimethylethyl 3-(4-amino-5-bromo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-1-azetidinecarboxylate (538 mg) in 78% purity. LC-MS (ES) m/z=368.2, 370.2 [M+H]+.