Potassium Carbonate → 4-(2-butynyloxy)-6-(N-ethyl-N-isopropylamino)pyrimidine

HRID 1592171ノート

反応式

HRID 1592171 の反応式
Cl[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]#[C:11][CH3:12])[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19]([NH:21][CH:22]([CH3:24])[CH3:23])[CH3:20]>CN(C)C=O>[CH2:9]([O:8][C:6]1[CH:7]=[C:2]([N:21]([CH2:19][CH3:20])[CH:22]([CH3:24])[CH3:23])[N:3]=[CH:4][N:5]=1)[C:10]#[C:11][CH3:12]

参加物

5

反応物 3

HCID 11430Potassium Carbonate3 回HCID 88318Isopropylethylamine3 回HCID 121376024-(2-Butynyloxy)-6-chloropyrimidine

生成物 1

HCID 225997234-(2-butynyloxy)-6-(N-ethyl-N-isopropylamino)pyrimidine収率 33.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To 2 ml of N,N-dimethylformamide were added 183 mg of 4-chloro-6-(2-butynyloxy)pyrimidine, 166 mg of potassium carbonate, and 87 mg of N-ethylisopropylamine, followed by stirring at 60° C. for 7 hours. Then, 166 mg of potassium carbonate and 435 mg of N-ethylisopropylamine were added, and the mixture was stirred at 80° C. for 8 hours. Then, 166 mg of potassium carbonate and 435 mg of N-ethylisopropylamine were added, and the mixture was stirred at 120° C. for 5 hours. The reaction mixture was then left for cooling to room temperature and subjected to phase separation three times between ethyl acetate and an aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to preparative silica gel thin layer chromatography to give 79 mg of 4-(2-butynyloxy)-6-(N-ethyl-N-isopropylamino)pyrimidine (the present compound (105)).

後処理

  1. stirringthe mixture was stirred at 80° C. for 8 hours
  2. stirringthe mixture was stirred at 120° C. for 5 hours
  3. waitThe reaction mixture was then left
  4. temperaturefor cooling to room temperature
  5. customsubjected to phase separation three times between ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-ca65dded8548451db2beda9fcb0e7236
出典データセット
uspto-grants-2007_11
特許番号
US07291730B2

反応ノート

読み込み中…