Lithium Hydroxide → 2-tert-Butyl-4-{4-[3-(4-methyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-6-cyclobutylpyrimidine

HRID 219747노트

반응식

HRID 219747 반응식
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19]Cl)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:21]2[CH2:24][CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][N:26]1[CH:30]=[N:29][N:28]=[C:27]1[SH:31].[OH-].[Li+].[I-].[K+]>CN(C)C=O>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][S:31][C:27]3[N:26]([CH3:25])[CH:30]=[N:29][N:28]=3)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:21]2[CH2:24][CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 3939Lithium HydroxideHCID 4875Potassium IodideHCID 666731042-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclobutyl-pyrimidineHCID 178481306HCID 178481306, 화합물

생성물 1

HCID 115681542-tert-Butyl-4-{4-[3-(4-methyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-6-cyclobutylpyrimidine수율 47%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

0.8 g of 2-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclobutyl-pyrimidine (2.28 mmol), 0.29 g of 4-methyl-3-mercapto-1,2,4-triazole (2.52 mmol), 0.15 g of lithium hydroxide and a tip of a spatula of potassium iodide were dissolved in 20 ml of dimethylformamide. The mixture was stirred for 14 h at room temperature and then extracted with water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness. The residue was then purified by column chromatography on silica gel (dichloromethane-methanol (2-10%)) to yield an oily residue that was precipitated with acetonitrile thereby yielding 0.46 g of the title compound (47%).

후처리

  1. extractionextracted with water and ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was then purified by column chromatography on silica gel (dichloromethane-methanol (2-10%))
  6. customto yield an oily residue that
  7. customwas precipitated with acetonitrile

출처 및 근거

ORD 기록
ord-02dd9ebd37574f9fb31f0a290af4abce
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202868B2

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