Acetyl chloride → 5-[8-(4-Acetylpiperazin-1-yl)-9-isobutyl-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amine

HRID 421298

Reaktionsgleichung

Reaktionsgleichung von HRID 421298
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[CH2:12]([N:16]1[C:24]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[N:23][C:22]2[C:17]1=[N:18][C:19]([C:37]1[CH:38]=[N:39][C:40]([NH2:43])=[N:41][CH:42]=1)=[N:20][C:21]=2[N:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)[CH:13]([CH3:15])[CH3:14]>CN1CCCC1=O>[C:8]([N:28]1[CH2:27][CH2:26][N:25]([C:24]2[N:16]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:17]3[C:22]([N:23]=2)=[C:21]([N:31]2[CH2:32][CH2:33][O:34][CH2:35][CH2:36]2)[N:20]=[C:19]([C:37]2[CH:38]=[N:39][C:40]([NH2:43])=[N:41][CH:42]=2)[N:18]=3)[CH2:30][CH2:29]1)(=[O:10])[CH3:9]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 593335015-(9-Isobutyl-6-morpholino-8-(piperazin-1-yl)-9H-purin-2-yl)pyrimidin-2-amine

Produkt 1

HCID 453778625-[8-(4-Acetylpiperazin-1-yl)-9-isobutyl-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Triethylamine (143 μl) and acetyl chloride (50 μl 0.72 mmol) were added to 5-(9-isobutyl-6-morpholin-4-yl-8-piperazin-1-yl-9H-purin-2-yl)pyrimidin-2-amine (2 ml of solution of 100 mg of this compound in 1 ml of N-methylpyrrolidone) and the resulting mixture was stirred for 1 hour. The resulting mixture was partitioned with ethyl acetate and water and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was dissolved in methanol (2 ml) followed by the addition of 25% sodium methoxide-methanol solution (1 ml), and the resulting mixture was stirred for 3 hours. The reaction mixture was partitioned with ethyl acetate and water, the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. Dimethyl sulfoxide (3 ml) was added to the residue, then the resulting mixture was partitioned with ethyl acetate and water, the organic layer was similarly dried, and then the solvent was evaporated to give the title compound (150 mg, 61%) as a pale yellow solid.

Aufarbeitung

  1. customThe resulting mixture was partitioned with ethyl acetate and water
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in methanol (2 ml)
  5. additionfollowed by the addition of 25% sodium methoxide-methanol solution (1 ml)
  6. stirringthe resulting mixture was stirred for 3 hours
  7. customThe reaction mixture was partitioned with ethyl acetate and water
  8. dry with materialthe organic layer was dried over magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. additionDimethyl sulfoxide (3 ml) was added to the residue
  11. customthe resulting mixture was partitioned with ethyl acetate and water
  12. customthe organic layer was similarly dried
  13. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f2dc74035e5a4594870d687e050f4009
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097622B2

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