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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 1617212
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HRID 1617212 반응식
[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
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-967dad76572547b8be227e182699cf65
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08765939B2

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