反应 #2171077

反应方程式

4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]aniline hydrochloride

2-chloro-4-(indolin-1-yl)pyrimidine

butanol

→

product

收率 64.4%

2-{4-[2-Hydroxy-3-(N,N-dimethylamino)propoxy]anilino}-4-(indolin-1-yl)pyrimidine

收率 64.4%

溶剂

methanol

—

ii

反应条件

后处理

1. 1
   workup.ADDITIONsilica (1 g) was added
2. 2
   其他Volatile material was removed by evaporation
3. 3
   其他the residue was purified by column chromatography
4. 4
   洗涤eluting with 0-5% 2.0M methanolic ammonia solution in DCM

实验过程

A hot solution of 4-[2-hydroxy-3-(N,N-dimethylamino)propoxy]aniline hydrochloride (Method 1, 219 mg, 0.77 mmol) in methanol (2 ml) was added to a solution of 2-chloro-4-(indolin-1-yl)pyrimidine (Method 3, 200 mg, 0.86 mmol) in ii-butanol (20 ml). The mixture was heated at 100° C. for 18 hours and silica (1 g) was added. Volatile material was removed by evaporation and the residue was purified by column chromatography, eluting with 0-5% 2.0M methanolic ammonia solution in DCM, to give the product as a colourless solid (201 mg, 61%). NMR: 2.19 (s, 6H), 2.21-2.3 (m, 1H), 2.3-2.4 (m, 1H), 3.1-3.25 (m, 2H), 3.8-4.1 (m, 5H), 5.75 (m, 1H), 6.2 (m, 2H), 6.8-6.9 (m, 3H), 7.0-7.1 (m, 1H), 7.15-7.25 (m, 1H), 7.5-7.6 (m, 2H), 8.05-8.1 (m, 1H), 8.3-8.4 (m, 1H), 8.95 (s, 1H); MS (MH+): 406.5.

来源