Ethyl Acetate → (4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-fluorophenyl)methanol

HRID 1617163ノート

反応式

HRID 1617163 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[CH:12][C:11]=2[F:20])=[C:4]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOC(C)=O.[OH-].[Na+]>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:19]=[CH:18][C:13]([CH2:14][OH:15])=[CH:12][C:11]=2[F:20])=[C:4]([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[N:3]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66819400Methyl 4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-fluorobenzoate

生成物 1

HCID 66819207(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-fluorophenyl)methanol収率 60.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of the product from step (iv) (1.52 g) in THF (30 mL) was added portionwise to a stirred solution of lithium aluminium hydride (1M in THF; 8.43 mL) in THF (30 mL) at 0° C. under nitrogen. The resulting mixture was stirred at rt for 2 h. EtOAc (10 mL) was added cautiously to the reaction mixture and the mixture added portionwise to 2M NaOH (100 mL). The mixture was stirred for 30 min and the aqueous solution was extracted with EtOAc. The combined organic phase was dried, filtered and evaporated. The crude product was purified by chromatography elutinhg with 2 to 5% MeOH in acetonitrile to give the subtitle compound as a yellow oil 0.85 g.

後処理

  1. stirringThe mixture was stirred for 30 min
  2. extractionthe aqueous solution was extracted with EtOAc
  3. customThe combined organic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by chromatography elutinhg with 2 to 5% MeOH in acetonitrile

出典と根拠

ORDレコード
ord-33a44b5d478f4faa901d647153ec9c4c
出典データセット
uspto-grants-2014_07
特許番号
US08765939B2

反応ノート

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