Potassium Cyanide → 2-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-fluorophenyl)acetonitrile

HRID 1617165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1617165
[C-:1]#[N:2].[K+].Cl[CH2:5][C:6]1[CH:26]=[CH:25][C:9]([CH2:10][C:11]2[C:12]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[N:13][C:14]([NH2:18])=[N:15][C:16]=2[CH3:17])=[C:8]([F:27])[CH:7]=1>CS(C)=O.CN(C=O)C.CCOC(C)=O>[NH2:18][C:14]1[N:15]=[C:16]([CH3:17])[C:11]([CH2:10][C:9]2[CH:25]=[CH:26][C:6]([CH2:5][C:1]#[N:2])=[CH:7][C:8]=2[F:27])=[C:12]([NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[N:13]=1

Komponenten

6

Edukt 2

HCID 9032Potassium CyanideHCID 689525035-(4-(Chloromethyl)-2-fluorobenzyl)-6-methyl-N4-pentylpyrimidine-2,4-diamine

Produkt 1

HCID 684148972-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-fluorophenyl)acetonitrileAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Potassium cyanide (0.473 g) was added to a stirred solution of the product from step (vi) (0.85 g) in DMSO (10 mL) and DMF (10 mL). The mixture was stirred at rt for 15 h, diluted with EtOAc, washed with saturated NaHCO3 solution, saturated brine dried, filtered and evaporated. The crude product was purified by chromatography eluting with 0 to 5% MeOH in DCM to afford the subtitle compound as a yellow solid 0.530 g.

Aufarbeitung

  1. washwashed with saturated NaHCO3 solution, saturated brine
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified by chromatography
  6. washeluting with 0 to 5% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-c58396bbe3944e639099aaaf25c134dd
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765939B2

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