Triethylamine → 4-Chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine

HRID 624765ノート

反応式

HRID 624765 の反応式
[CH3:1][S:2][C:3]1[NH:8][C:7](=O)[N:6]2[N:10]=[CH:11][CH:12]=[C:5]2[N:4]=1.P(Cl)(Cl)([Cl:15])=O.C(N(CC)CC)C>C(#N)C>[Cl:15][C:7]1[N:6]2[N:10]=[CH:11][CH:12]=[C:5]2[N:4]=[C:3]([S:2][CH3:1])[N:8]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1354442592-(Methylthio)pyrazolo[1,5-a][1,3,5]triazin-4(3H)-one

生成物 1

HCID 129161154-Chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine収率 71%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

In a round bottom flask equipped with a magnetic stirbar, 2-(methylthio)pyrazolo[1,5-a][1,3,5]triazin-4(3H)-one (1.0 eq, 10.43 g, 57.24 mmol) was suspended in acetonitrile (100 ml). Phosphorus oxychloride (4.0 eq, 21 ml, 229.4 mmol) and triethylamine (1.05 eq, 8.4 ml, 60.27 mmol) were added and the mixture stirred at reflux for 3.5 hours, at which time LCMS indicated completion of the reaction. The mixture was cooled down and slowly poured into crushed ice (final total volume of about 600 ml). The solid was filtered, washed with water and dried in a vacuum oven to afford 4-chloro-2-(methylthio)pyrazolo[1,5-a][1,3,5]triazine as a tan solid (8.15 g, 71% yield). LCMS (ES): >97% pure, m/z 201 [M+H]+.

後処理

  1. temperatureat reflux for 3.5 hours, at which time LCMS
  2. customcompletion of the reaction
  3. temperatureThe mixture was cooled down
  4. additionslowly poured
  5. custominto crushed ice (final total volume of about 600 ml)
  6. filtrationThe solid was filtered
  7. washwashed with water
  8. customdried in a vacuum oven

出典と根拠

ORDレコード
ord-cd77b86bfe6c48ef917c8241596b5ffa
出典データセット
uspto-grants-2016_04
特許番号
US09303033B2

反応ノート

読み込み中…