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1-Butanol → (S)-Methyl 2-(3-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-4-fluorophenyl)acetate

HRID 2387864
ノート
印刷プレビュー

反応式

HRID 2387864 の反応式
[OH-:1].[K+].[NH2:3][C:4]1[N:9]=[C:8]([NH:10][C@@H:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][OH:14])[C:7]([CH2:18][C:19]2[CH:20]=[C:21]([CH2:26][C:27]#N)[CH:22]=[CH:23][C:24]=2[F:25])=[C:6]([CH3:29])[N:5]=1.Cl.[CH2:31]([OH:35])CCC>O>[NH2:3][C:4]1[N:9]=[C:8]([NH:10][C@@H:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][OH:14])[C:7]([CH2:18][C:19]2[CH:20]=[C:21]([CH2:26][C:27]([O:35][CH3:31])=[O:1])[CH:22]=[CH:23][C:24]=2[F:25])=[C:6]([CH3:29])[N:5]=1
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

6

反応物 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 68956027(S)-2-(3-((2-Amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-4-fluorophenyl)acetonitrile

生成物 1

HCID 42613317(S)-Methyl 2-(3-((2-amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)-4-fluorophenyl)acetate

試薬・触媒・溶媒 1

HCID 962
Water
溶媒

反応条件

温度
100 °C

実験手順

Aq. 5M KOH (0.5 mL) was added to a stirred solution of the product from step (v) (70 mg) in butan-1-ol (1 mL) and heated to 100° C. for 15 h. The mixture was allowed to cool, diluted with water (2 mL) and then adjusted to ˜pH 7 with conc. HCl. The organic phase was separated and the aqueous was extracted with butan-1-ol (5 mL). The combined organic extracts were evaporated, the residue was dissolved in MeOH and conc. HCl (0.3 mL) was added and the mixture heated to 70° C. for 1 h. After cooling the reaction was poured into sat. NaHCO3 (10 mL) and extracted with EtOAc, dried and the solvent removed. The crude product was purified by RPHPLC to afford the title compound as a colourless gum, 22 mg.

後処理

  1. temperatureto cool
  2. customThe organic phase was separated
  3. extractionthe aqueous was extracted with butan-1-ol (5 mL)
  4. customThe combined organic extracts were evaporated
  5. dissolutionthe residue was dissolved in MeOH
  6. additionconc. HCl (0.3 mL) was added
  7. temperaturethe mixture heated to 70° C. for 1 h
  8. temperatureAfter cooling the reaction
  9. additionwas poured into sat. NaHCO3 (10 mL)
  10. extractionextracted with EtOAc
  11. customdried
  12. customthe solvent removed
  13. customThe crude product was purified by RPHPLC

出典と根拠

ORDレコード
ord-88a6fa16b0554a0a9a693f83cbb6f42b
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08268990B2

反応ノート

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