4-(Chloromethyl)pyrimidine → 2-(Pyrimidin-4-ylmethyl)isoindoline-1,3-dione

HRID 560558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 560558
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][N:4]=1.[C:9]1(=[O:19])[NH:13][C:12](=[O:14])[C:11]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:10]12.[K]>CN(C)C=O>[N:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:13]2[C:9](=[O:19])[C:10]3[C:11](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:12]2=[O:14])=[N:4][CH:5]=1

Komponenten

4

Edukt 2

HCID 131235534-(Chloromethyl)pyrimidineHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 666302422-(Pyrimidin-4-ylmethyl)isoindoline-1,3-dioneAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(chloromethyl)pyrimidine (4.10 g, 31.9 mmol, prepared according to R. W. Carling et al., J. Med. Chem., (2004), Vol. 47, pp. 1807-1822) and potassium phthalimide (5.91 g, 31.89 mmol) in N,N-dimethylformamide (60 mL) was heated to 110° C. for 16 hours. The reaction mixture was cooled to ambient temperature, and concentrated in vacuo. The residue was dissolved in dichloromethane (100 mL), washed with water (50 mL) and brine (50 ml). The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with 40-50% ethyl acetate in hexanes to afford 2-(pyrimidin-4-ylmethyl)isoindoline-1,3-dione in 40% yield (3.0 g): 1HNMR (300 MHz, CDCl3) δ 9.13 (s, 1H), 8.70 (br s, 1H), 7.93-7.86 (m, 2H), 7.79-7.75 (m, 2H), 7.30 (d, J=6.0 Hz, 1H), 4.99 (s, 2H): MS (ES+) m/z 240.1 (M+1).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  3. washwashed with water (50 mL) and brine (50 ml)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluted with 40-50% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5f6b2a3f2d5c4567b0f343e7e035936c
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063084B2

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