Acetone → Deferiprone

HRID 331110

Reaction equation

HRID 331110 reaction equation
[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]

Participants

5

Reactant 3

HCID 180AcetoneHCID 7922Succinic anhydrideHCID 79782-Aminopyrimidine

Product 1

HCID 2972DeferiproneYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-667df60da1de4860a421f74428d4bef0
Source dataset
uspto-grants-2014_11
Patent number
US08877766B2

Linked notes

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