聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 5-chloro-N-(3,4,5-trimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine

HRID 1410106笔记

反应方程式

HRID 1410106 反应方程式
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH2:24])[CH:17]=[C:18]([O:22][CH3:23])[C:19]=1[O:20][CH3:21].CCN(C(C)C)C(C)C.O>CS(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([NH:24][C:16]2[CH:17]=[C:18]([O:22][CH3:23])[C:19]([O:20][CH3:21])=[C:14]([O:13][CH3:12])[CH:15]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1

参与物

6

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 322853,4,5-三甲氧基苯胺HCID 81531N,N-二异丙基乙胺HCID 6096395,7-二氯噻唑并[5,4-D]嘧啶

产物 1

HCID 866717915-chloro-N-(3,4,5-trimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine收率 98.6%

试剂、催化剂与溶剂 1

HCID 679二甲基亚砜溶剂

实验过程

To a stirred solution of 5,7-dichlorothiazolo[5,4-d]pyrimidine (200 mg, 0.97 mmol) and 3,4,5-trimethoxybenzenamine (230 mg, 1.25 mmol) in 7 mL of DMSO was added DIEA (188 mg, 1.45 mmol) in one portion at room temperature. Then the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into 40 mL of water, and the solid obtained was filtered, washed with water (10 mL) to give a crude product. It was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate) to give 5-chloro-N-(3,4,5-trimethoxyphenyl)thiazolo[5,4-d]pyrimidin-7-amine (337 mg, 98.6%) as a yellow solid. LC-MS: 353.0 [M+H]+, 726.9 [2M+H]+, tR=1.56 min.

后处理

  1. customthe solid obtained
  2. filtrationwas filtered
  3. washwashed with water (10 mL)
  4. customto give a crude product
  5. customIt was purified by silica gel chromatography (silica gel 200-300 mesh, eluting with ethyl acetate)

来源与证据

ORD记录
ord-bb5fa45fc6f147d8a0386ec0810a570d
来源数据集
uspto-grants-2014_12
专利号
US08921383B2

反应笔记

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