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

HRID 2291663ノート

反応式

HRID 2291663 の反応式
[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

参加物

3

反応物 2

HCID 713FormamideHCID 14050402Methyl 3-amino-5-chloro-2-thiophenecarboxylate

生成物 1

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

反応条件

温度
205 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3d47ed57a50c4a52a4de07c285b23e88
出典データセット
uspto-grants-1989_01
特許番号
US04797486

反応ノート

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