Lithium Hydroxide → 2-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetonitrile

HRID 445054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445054
FC(F)(F)C(O)=O.[NH2:8][C:9]1[N:14]=[C:13](OS(C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)(=O)=O)[C:12]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([CH2:41][C:42]#[N:43])=[CH:37][CH:36]=2)=[C:11]([CH3:44])[N:10]=1.[CH2:45]([NH2:50])[CH2:46][CH2:47][CH2:48][CH3:49].[Li+].[OH-]>C(OCCCC)(=O)C.C1(C)C=CC=CC=1.C1COCC1>[NH2:8][C:9]1[N:10]=[C:11]([CH3:44])[C:12]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([CH2:41][C:42]#[N:43])=[CH:39][CH:40]=2)=[C:13]([NH:50][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])[N:14]=1

Komponenten

8

Edukt 4

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 8060PentylamineHCID 866479282-(4-((2-Amino-4-((2,4,6-triisopropylbenzenesulfonyl)oxy)-6-methylpyrimidin-5-yl)methyl)phenyl)acetonitrile

Produkt 1

HCID 595906382-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittelHCID 31272Butyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Trifluoroacetic acid (2.19 g, 19.2 mmol) was added to a suspension of the product from step (iii) (10.0 g, 19.2 mmol) and n-pentylamine (5.0 g, 57.6 mmol) in butyl acetate (65.0 g), and the mixture was heated at 120° C. for 6 hours. The mixture was cooled and concentrated under reduced pressure to give a solid. A suspension of the solid in toluene (30.0 g) was concentrated under reduced pressure again to give a solid. 5% aq. LiOH (60.0 g) was added to the solution of the solid in toluene (55.0 g) and THF (14.0 g), and the mixture was stirred at 40° C. The separated organic layer was washed with water (60.0 g) at 40° C. and concentrated under reduced pressure to afford a solid. A suspension of the obtained solid in toluene (42.0 g) was stirred at 54° C. for 1 hour and cooled to 5° C. and stirred at 5° C. for 10 hours. The resulting precipitate was collected by filtration and washed with acetonitrile (5.0 g) and water (12.0 g) respectively to give the subtitle compound as wet crystals. 5.90 g. This product was used in the next step without desiccation.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. customto give a solid
  4. concentrationwas concentrated under reduced pressure again
  5. customto give a solid
  6. washThe separated organic layer was washed with water (60.0 g) at 40° C.
  7. concentrationconcentrated under reduced pressure
  8. customto afford a solid
  9. temperaturecooled to 5° C.
  10. stirringstirred at 5° C. for 10 hours
  11. filtrationThe resulting precipitate was collected by filtration
  12. washwashed with acetonitrile (5.0 g) and water (12.0 g) respectively

Quellen und Nachweise

ORD-Eintrag
ord-7d82d27bf1b449cb9f75e5d08578c4a2
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476288B2

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