Triethylamine → 2-Chloro-4-(trans-cinnamylamino)-7-methylthieno[3,2-d]pyrimidine

HRID 1250671ノート

反応式

HRID 1250671 の反応式
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.C(N(CC)CC)C.Cl.[CH2:21]([NH2:30])/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:30][CH2:21]/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 6444486Cinnamylamine hydrochloride, (E)-HCID 71470642,4-Dichloro-7-methylthieno(3,2-d)pyrimidine

生成物 1

HCID 183264422-Chloro-4-(trans-cinnamylamino)-7-methylthieno[3,2-d]pyrimidine収率 54%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To 10 ml of a solution of 438 mg (2.0 mmol) of 2,4-dichloro-7-metylthieno[3,2-d]pyrimidine and 445 mg (4.4 mmol) of triethylamine in DMF was added 339 mg (2.0 mmol) of trans-cinnamylamine hydrochloride under ice cooling. The reaction mixture was stirred at the same temperature for one hour and then allowed to resume room temperature, followed by stirring for further 2 hours. After completion of the reaction, ice water was added to the reaction mixture, followed by extraction with ethyl acetate (50 ml×3). After the organic layer was washed successively with 1N hydrochloric acid, water and brine and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/4) to give 341 mg (yield: 54.0%) of the title compound.

後処理

  1. customto resume room temperature
  2. stirringby stirring for further 2 hours
  3. additionwas added to the reaction mixture
  4. extractionfollowed by extraction with ethyl acetate (50 ml×3)
  5. washAfter the organic layer was washed successively with 1N hydrochloric acid, water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/4)

出典と根拠

ORDレコード
ord-0647b7b1a30c4fd8b9cb64434c290bb1
出典データセット
uspto-grants-2002_01
特許番号
US06339089B2

反応ノート

読み込み中…