Ethyl Acetate → Ethyl 5-((5-fluoropyridin-3-yl)amino)-3-(methylthio)-1,2,4-triazine-6-carboxylate

HRID 577424ノート

反応式

HRID 577424 の反応式
Cl[C:2]1[N:3]=[C:4]([S:13][CH3:14])[N:5]=[N:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[NH2:15][C:16]1[CH:17]=[N:18][CH:19]=[C:20]([F:22])[CH:21]=1.CCN(C(C)C)C(C)C.CCOC(C)=O>CN(C=O)C>[F:22][C:20]1[CH:21]=[C:16]([NH:15][C:2]2[N:3]=[C:4]([S:13][CH3:14])[N:5]=[N:6][C:7]=2[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:17]=[N:18][CH:19]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 5744505-Fluoro-3-pyridinamineHCID 11557703Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-Carboxylate

生成物 1

HCID 86706418Ethyl 5-((5-fluoropyridin-3-yl)amino)-3-(methylthio)-1,2,4-triazine-6-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (300 mg, 1.29 mmol) was dissolved in 10 mL dry DMF. To it was added 3-amino-5-fluoropyridine (728 mg, 6.50 mmol) and then DIEA (0.45 mL, 2.60 mmol). The mixture was stirred at 100° C. for 1.5 h. To the mixture were poured 200 mL EtOAc. The mixture was washed with brine twice and water twice, dried in MgSO4, and concentrated in vacuo to afford crude ethyl 5-((5-fluoropyridin-3-yl)amino)-3-(methylthio)-1,2,4-triazine-6-carboxylate. It was stirred in 30 mL “7.0 N ammonia in methanol” (Acros, #133710010) as a slurry for overnight. The solid was isolated by filtration, washed with hexane and dried in vacuum oven. It was very pure 5-((5-fluoropyridin-3-yl)amino)-3-(methylthio)-1,2,4-triazine-6-carboxamide. Yield was 189 mg (52% for 2 steps).

後処理

  1. washThe mixture was washed with brine twice
  2. dry with materialwater twice, dried in MgSO4
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-08d6695a8b7e48fb83509069f9e2ed10
出典データセット
uspto-grants-2015_05
特許番号
US09040530B2

反応ノート

読み込み中…