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Potassium Hydroxide → 4-((2-Ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenol

HRID 403485
ノート
印刷プレビュー

反応式

HRID 403485 の反応式
[OH-:1].[K+].Br[C:4]1[CH:23]=[CH:22][C:7]([CH2:8][C:9]2[C:10]([CH2:20][CH3:21])=[N:11][N:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[N:14][C:13]=23)=[CH:6][CH:5]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:20]([C:10]1[C:9]([CH2:8][C:7]2[CH:22]=[CH:23][C:4]([OH:1])=[CH:5][CH:6]=2)=[C:13]2[N:14]=[C:15]([CH3:19])[CH:16]=[C:17]([CH3:18])[N:12]2[N:11]=1)[CH3:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 683789033-(4-Bromobenzyl)-2-ethyl-5,7-dimethylpyrazolo[1,5-A]pyrimidine

生成物 1

HCID 683792244-((2-Ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenol

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
100 °C

実験手順

Potassiumhydroxide (1.96 g, 34.9 mmol) was dissolved in 30 ml of a 1:1 mixture of argon-flushed dioxane and water. After addition of 3-(4-bromo-benzyl)-2-ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidine (3) (4 g, 11.62 mmol), Pd2(dba)3 (426 mg, 0.465 mmol) and tetramethyl Xphos (894 mg, 1.859 mmol), the mixture was flushed with argon and stirred for 1 h at 100° C. Then the mixture was treated with 1N HCl and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2 SO4 and evaporated. Purification by chromatography (silica gel, ethylaceta/n-heptane) gave a yellow solid.

後処理

  1. customflushed dioxane and water
  2. customthe mixture was flushed with argon
  3. additionThen the mixture was treated with 1N HCl
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. customdried over Na2 SO4
  7. customevaporated
  8. customPurification by chromatography (silica gel, ethylaceta/n-heptane)
  9. customgave a yellow solid

出典と根拠

ORDレコード
ord-878f69bebbad48dba2d8c12d0f021e7d
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08748435B2

反応ノート

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