1-Butanol → (s)-2-(4-((2-Amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)phenyl)acetic acid

HRID 1617252

Reaktionsgleichung

Reaktionsgleichung von HRID 1617252
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][C:10]2[CH:15]=[CH:14]C(CC#N)=C[CH:11]=2)=[C:4]([CH3:19])[N:3]=1.[NH2:20][C@@H:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][OH:24].[OH-:28].[K+].[CH2:30]([OH:34])[CH2:31][CH2:32][CH3:33]>>[NH2:1][C:2]1[N:7]=[C:6]([NH:20][C@@H:21]([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][OH:24])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:32]([CH2:31][C:30]([OH:28])=[O:34])=[CH:33][CH:11]=2)=[C:4]([CH3:19])[N:3]=1

Komponenten

5

Edukt 4

HCID 2631-ButanolHCID 14797Potassium HydroxideHCID 11062353(S)-3-aminohexan-1-olHCID 874447822-(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)phenyl)acetonitrile

Produkt 1

HCID 68957300(s)-2-(4-((2-Amino-4-(1-hydroxyhexan-3-ylamino)-6-methylpyrimidin-5-yl)methyl)phenyl)acetic acid

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of the product of example 81 step (iii) (0.4 g) and (S)-3-aminohexan-1-ol (0.5 g) in butan-1-ol (3 mL) was sealed into a microwave tube. The reaction was performed in the CEM Microwave, at 160° C. and 100 W for 1.5 h. Aq. 5M KOH (iml) was added and the mixture heated at 100° C. for 48 h. The mixture was cooled and the solvent evaporated under reduced pressure. The residue was purified by RPHPLC to give the subtitle compound, 174 mg.

Aufarbeitung

  1. customwas sealed into a microwave tube
  2. customwas performed in the CEM Microwave, at 160° C.
  3. temperatureThe mixture was cooled
  4. customthe solvent evaporated under reduced pressure
  5. customThe residue was purified by RPHPLC

Quellen und Nachweise

ORD-Eintrag
ord-9d98d595517e4862b82eace92a89943c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765939B2

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