(2S)-2-aminopentan-1-ol → (S)-2-(4-((2-Amino-4-(1-hydroxypentan-2-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

HRID 1617174

Reaktionsgleichung

Reaktionsgleichung von HRID 1617174
[NH2:1][C@@H:2]([CH2:5][CH2:6][CH3:7])[CH2:3][OH:4].[NH2:8][C:9]1[N:14]=[C:13](Cl)[C:12]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]#[N:25])=[CH:19][C:18]=2[O:26][CH3:27])=[C:11]([CH3:28])[N:10]=1>CN1C(=O)CCC1.CCOC(C)=O>[NH2:8][C:9]1[N:14]=[C:13]([NH:1][C@@H:2]([CH2:5][CH2:6][CH3:7])[CH2:3][OH:4])[C:12]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]#[N:25])=[CH:19][C:18]=2[O:26][CH3:27])=[C:11]([CH3:28])[N:10]=1

Komponenten

5

Edukt 2

HCID 6951248(2S)-2-aminopentan-1-olHCID 866334022-(4-((2-Amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

Produkt 1

HCID 68955240(S)-2-(4-((2-Amino-4-(1-hydroxypentan-2-ylamino)-6-methylpyrimidin-5-yl)methyl)-3-methoxyphenyl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

(S)-2-Aminopentan-1-ol (0.136 g) was added to a solution of the product from step (iii) in NMP (2 mL). The resulting mixture was stirred at 140° C. for 50 h then diluted with EtOAc and washed with saturated NaHCO3 solution and saturated brine. The organic phase was dried, filtered and evaporated. The crude product was purified by column chromatography, elution gradient 5 to 10% MeOH in DCM to give the subtitle compound, 0.095 g.

Aufarbeitung

  1. washwashed with saturated NaHCO3 solution and saturated brine
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by column chromatography, elution gradient 5 to 10% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-6913b3a48b284ac8ad14246b53620be3
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765939B2

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