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

HRID 2291663노트

반응식

HRID 2291663 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

반응 조건

온도
205 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3d47ed57a50c4a52a4de07c285b23e88
출처 데이터셋
uspto-grants-1989_01
특허 번호
US04797486

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