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

HRID 624765노트

반응식

HRID 624765 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-cd77b86bfe6c48ef917c8241596b5ffa
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303033B2

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