Diisopropylethylamine → 4-chloro-6-(1-trimethylsilanylmethyl-1H-[1,2,3]triazol-4-yl)-thieno[3,2-d]pyrimidine

HRID 1818944ノート

反応式

HRID 1818944 の反応式
[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:11]#[CH:12])=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:13][Si:14]([CH2:17][N:18]=[N+:19]=[N-:20])([CH3:16])[CH3:15].CCN(C(C)C)C(C)C>CN(C=O)C.[Cu]I>[Cl:1][C:2]1[C:3]2[S:10][C:9]([C:11]3[N:20]=[N:19][N:18]([CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[CH:12]=3)=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 150751Trimethylsilylmethyl AzideHCID 599822624-Chloro-6-ethynylthieno[3,2-d]pyrimidine

生成物 1

HCID 866031744-chloro-6-(1-trimethylsilanylmethyl-1H-[1,2,3]triazol-4-yl)-thieno[3,2-d]pyrimidine

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of compound 48.2 (1.0 mmol), trimethylsilylmethyl azide (5.0 mmol), CuI (0.2 mmol), and DIEA (1.0 mmol) in DMF (10 mL) was stirred at room temperature for 24 hours. The solvent was removed and the residue was diluted with water and extracted with EtOAc. The organic layer was washed with dilute aqueous ammonium hydroxide, brine, dried, concentrated and purified by flash column chromatography to provide 4-chloro-6-(1-trimethylsilanylmethyl-1H-[1,2,3]triazol-4-yl)-thieno[3,2-d]pyrimidine (compound 48.3) in 80% yield. EIMS (m/z): calcd. for C12H14ClN5SSi (M+)+H 324.04. found 324.00.

後処理

  1. customThe solvent was removed
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with dilute aqueous ammonium hydroxide, brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified by flash column chromatography

出典と根拠

ORDレコード
ord-8b26ec62de9b49de941f348354d2e8d4
出典データセット
uspto-grants-2009_10
特許番号
US07601725B2

反応ノート

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