Acetylacetone → 5,7-Dimethyl-2-(methylsulfanyl)-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1752790ノート

反応式

HRID 1752790 の反応式
[CH3:1][C:2](=O)[CH2:3][C:4](=O)[CH3:5].[NH2:8][C:9]1[N:13]=[C:12]([S:14][CH3:15])[NH:11][N:10]=1>C(O)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH3:5])[N:10]2[N:11]=[C:12]([S:14][CH3:15])[N:13]=[C:9]2[N:8]=1

参加物

4

反応物 2

HCID 31261AcetylacetoneHCID 178503514HCID 178503514、化合物2 回

生成物 1

HCID 7066025,7-Dimethyl-2-(methylsulfanyl)-[1,2,4]triazolo[1,5-a]pyrimidine収率 71.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
135 °C

実験手順

A mixture of 2,4-pentanedione (11.54 g, 115 mmol), 3-amino-5-methylthio-1H-1,2,4-triazole (15.0 g, 115 mmol), and glacial acetic acid (115 mL) was added to a 1 L RBF with a magnetic stirring bar. The flask was fitted with a condenser, and warmed in an oil bath to a gentle reflux at 135° C. The mixture was heated for 15 hours. Progress of the reaction was monitored by analytical HPLC with UV detection at 215 and 254 nm. The starting material 3-amino-5-methylthio-1H-1,2,4-triazole elutes rapidly with retention time of 0.7 min, and the product elutes with retention time of 5.0 min. The mixture was cooled to room temperature, then slowly poured into stirring ice/water (750 mL) to precipitate product and stirred ˜20 minutes. Solids were isolated by filtration, rinsed with 250 mL of water, and then dried under reduced pressure to afford the title compound as a powder (15.9 g, 71% yield).

後処理

  1. additionwas added to a 1 L RBF with a magnetic stirring bar
  2. customThe flask was fitted with a condenser
  3. temperaturewarmed in an oil bath to
  4. temperatureThe mixture was heated for 15 hours
  5. temperatureThe mixture was cooled to room temperature
  6. additionslowly poured
  7. customto precipitate product
  8. customSolids were isolated by filtration
  9. washrinsed with 250 mL of water
  10. customdried under reduced pressure

出典と根拠

ORDレコード
ord-5c3bee075a4e4643b613eacd832ca740
出典データセット
uspto-grants-2015_10
特許番号
US09163027B2

反応ノート

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