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

HRID 219751ノート

反応式

HRID 219751 の反応式
[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[CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:24][N:25]1[CH:29]=[N:28][N:27]=[C:26]1[SH:30].[OH-:31].[Li+].[I-].[Na+].CN(C)C=[O:38]>>[C:23]([OH:38])(=[O:31])[CH3:21].[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:30][C:26]3[N:25]([CH3:24])[CH:29]=[N:28][N:27]=3)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:21]2[CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 5

HCID 3939Lithium HydroxideHCID 5238Sodium IodideHCID 6228DimethylformamideHCID 690261252-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclopropyl-pyrimidineHCID 178481306HCID 178481306、化合物

生成物 1

HCID 690760382-tert-Butyl-4-{4-[3-(4-methyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-6-cyclopropyl-pyrimidine acetate

反応条件

温度
70 °C

実験手順

0.7 g of 2-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclopropyl-pyrimidine (1.45 mmol) and 0.55 g of 4-methyl-4H-[1,2,4]triazole-3-thiol (2.08 mmol) were dissolved in 10 ml of dimethylformamide. After addition of 0.104 g of lithium hydroxide (4.36 mmol) and 0.109 g of sodium iodide (0.73 mmol), the reaction mixture was stirred at 70° C. for 3 h. After cooling, the solvent was evaporated and the residue partitioned between dichloromethane and half-saturated sodium chloride solution. The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated. The residue was purified via preparative HPLC on a C18-Symmetry column (Waters) with water/methanol (0.1% acetic acid). Fractions containing the product were combined and lyophilised to yield 0.075 g of the product.

後処理

  1. temperatureAfter cooling
  2. customthe solvent was evaporated
  3. customthe residue partitioned between dichloromethane and half-saturated sodium chloride solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified via preparative HPLC on a C18-Symmetry column (Waters) with water/methanol (0.1% acetic acid)
  8. additionFractions containing the product

出典と根拠

ORDレコード
ord-ab2aa95b5690499ba8b774fa342168e1
出典データセット
uspto-grants-2012_06
特許番号
US08202868B2

反応ノート

読み込み中…