Acetone → Deferiprone

HRID 331110

Reaktionsgleichung

Reaktionsgleichung von HRID 331110
[C:1]1(=[O:7])O[C:4](=O)[CH2:3][CH2:2]1.N[C:9]1N=C[CH:12]=[CH:11][N:10]=1.CC(C)=[O:17]>C1(C)C=CC=CC=1>[CH3:12][C:11]1[N:10]([CH3:9])[CH:4]=[CH:3][C:2](=[O:17])[C:1]=1[OH:7]

Komponenten

5

Edukt 3

HCID 180AcetoneHCID 7922Succinic anhydrideHCID 79782-Aminopyrimidine

Produkt 1

HCID 2972DeferiproneAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Referring to FIG. 3, to 42.0 g (0.42 mol) of succinic anhydride (17) dissolved in 300 mL of toluene was added 20 g (0.21 mol) of 2-aminopyrimidine (21), (0.21 mol) dissolved in 200 mL of acetone, and the mixture was heated to 85° C. for 3 days. After cooling to r.t. (room temperature), the product precipitated and was filtrated and washed with toluene. The filtrate was dried in vacuo, and the dried product was then dissolved in 300 mL of anhydrous Ac2O and again heated to 85° C. for 3 hrs. After removal of the remaining Ac2O under vacuum, the product was purified by silica gel column chromatograph with CHCl3 and recrystallized from EtOAc to give HK-1 as a white solid, mp 148.5-149.5° C. in 32% yield. 1H NMR (CDCl3) δ 8.92 (d, J=4.88 Hz, 2H), 7.42 (t, J=4.88 Hz, 1H), 2.96 (s, 4H); Anal. Calcd for C8H7N3O2; C, 54.24; H, 3.98; N, 23.72. Found: C, 54.29; H, 4.19; N, 23.90.

Aufarbeitung

  1. temperatureAfter cooling to r.t. (room temperature)
  2. customthe product precipitated
  3. filtrationwas filtrated
  4. washwashed with toluene
  5. customThe filtrate was dried in vacuo
  6. dissolutionthe dried product was then dissolved in 300 mL of anhydrous Ac2O
  7. temperatureagain heated to 85° C. for 3 hrs
  8. customAfter removal of the remaining Ac2O under vacuum
  9. customthe product was purified by silica gel column chromatograph with CHCl3
  10. customrecrystallized from EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-667df60da1de4860a421f74428d4bef0
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877766B2

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