Formamide → 6-chlorothieno[3,2-d]pyrimidin-4(3H)-one

HRID 2291663笔记

反应方程式

HRID 2291663 反应方程式
[NH2:1][C:2]1[CH:6]=[C:5]([Cl:7])[S:4][C:3]=1[C:8]([O:10]C)=O.[CH:12]([NH2:14])=O>>[Cl:7][C:5]1[S:4][C:3]2[C:8](=[O:10])[NH:14][CH:12]=[N:1][C:2]=2[CH:6]=1

参与物

3

反应物 2

HCID 713FormamideHCID 140504023-氨基-5-氯噻吩-2-羧酸甲酯

产物 1

HCID 1355834876-chlorothieno[3,2-d]pyrimidin-4(3H)-one

反应条件

温度
205 °C

实验过程

In a 50 ml round bottom flask equipped with a mechanical stirrer and a reflux condenser, a mixture of 7.0 g (0.036 mole) of methyl 3-amino-5-chloro-2-thiophenecarboxylate and 15 ml of formamide was heated at 205° C. for 7 hours. Upon cooling to room temperature, the reaction solution afforded a precipitate which was filtered: yield about 3.3 g. The crude tan solid was taken up in hot methanol, treated with activated carbon, and filtered. Upon cooling to room temperature, the filtrate afforded yellow crystals of 6-chlorothieno[3,2-d]pyrimidin-4(3H)-one: m.p. 238°-239° C.; yield 2.5 g (36%); ir (KBr) 3427 cm-1, 1688, 1659, 1600, 1510, 1476, 1410 among others; 1H-nmr (CDCl3 +some trifluoroacetic acid) delta 7.5 ppm (s, 1H), 9.1 (s, 1H); mass spectrum 186 (molecular ion and parent peak with the expected isotope pattern), 159 (-27), 131 and others.

后处理

  1. customIn a 50 ml round bottom flask equipped with a mechanical stirrer and a reflux condenser
  2. temperatureUpon cooling to room temperature
  3. customthe reaction solution afforded a precipitate which
  4. filtrationwas filtered
  5. additiontreated with activated carbon
  6. filtrationfiltered
  7. temperatureUpon cooling to room temperature

来源与证据

ORD记录
ord-3d47ed57a50c4a52a4de07c285b23e88
来源数据集
uspto-grants-1989_01
专利号
US04797486

反应笔记

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