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

HRID 2067331노트

반응식

HRID 2067331 반응식
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

참가 물질

4

반응물 2

HCID 131235534-(Chloromethyl)pyrimidineHCID 24194345Phthalimide potassium salt

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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): 1H NMR (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).

후처리

  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

출처 및 근거

ORD 기록
ord-4091917eae29412dac28348f75185b01
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293768B2

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