反応 #1702125

反応方程式

NaHCO3

2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine

2,5-Dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine

3-methoxy-benzenamine

p-toluenesulfonic acid monohydrate

→

desired product

収率 34.7%

5-Chloro-N(4)-(3-methoxybenzyl)-N(2)-(3-methoxyphenyl)pyrimidine-2,4-diamine

収率 34.7%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   その他the organic solvent was removed under vacuum
2. 2
   抽出The aqueous layer was extracted with DCM twice
3. 3
   その他The combined organic layers were dried
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他The crude product was purified by silica gel column chromatography

実験手順

Into a reaction flask were added 2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine (0.20 g, 0.70 mmol) (prepared according to Example 1, step A), 1,4-dioxane (20 mL), 3-methoxy-benzenamine (0.13 g, 1.0 mmol), and p-toluenesulfonic acid monohydrate (49 mg, 0.26 mmol). The mixture was heated at 105° C. for 2 days. To the mixture was added an aqueous solution of NaHCO3 (saturated, 0.5 mL) and the organic solvent was removed under vacuum. The aqueous layer was extracted with DCM twice. The combined organic layers were dried, filtered and concentrated. The crude product was purified by silica gel column chromatography to provide the desired product (90 mg, 30%). LCMS for C19H20ClN4O2 (M+H)+: m/z=371.1.

出典