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

HRID 1818944노트

반응식

HRID 1818944 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8b26ec62de9b49de941f348354d2e8d4
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601725B2

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