3-{3-[5-Isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidine-4-carbonyl]-phenyl}-acrylonitrile → 3-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-phenyl]-acrylonitrile

HRID 426195Notes

Reaction equation

HRID 426195 reaction equation
[CH:1]([C:4]1[C:5]([C:30]([C:32]2[CH:33]=[C:34]([CH:38]=[CH:39][C:40]#[N:41])[CH:35]=[CH:36][CH:37]=2)=[O:31])=[N:6][C:7]([O:20]CC2C=CC(OC)=CC=2)=[N:8][C:9]=1[O:10]CC1C=CC(OC)=CC=1)([CH3:3])[CH3:2]>C(#N)C>[CH:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:20])[NH:6][C:5]=1[C:30]([C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]#[N:41])[CH:35]=[CH:36][CH:37]=1)=[O:31])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 667055543-{3-[5-Isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidine-4-carbonyl]-phenyl}-acrylonitrile

Product 1

HCID 667054933-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-phenyl]-acrylonitrileYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-{3-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidine-4-carbonyl]-phenyl}-acrylonitrile (1.25 g, 2.23 mmol) in acetonitrile (10 ml) at room temperature, was added ceric ammonium nitrate (3.67 g, 6.70 mmol) followed by distilled water (5 ml). After 3 hr., the reaction mixture was diluted with EA, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo to give a crude product as a white solid. The crude product was purified by silica gel column chromatography (eluent, EA:hexanes (4:1)) to afford 240 mg (35%) of a white solid. m.p. 210-211° C.; 1H NMR (200 MHz, CD3OD/CDCl3) δ 1.10 (6H, d, J=6.8 Hz), 2.39 (1H, m), 6.03 (1H, d, J=16.8 Hz), 7.45 (1H, d, J=16.8 Hz), 7.58 (3H, m), 8.01 (1H, s); m/z (LC/Mass, EI) 310 (M+H+).

Workup

  1. distillationby distilled water (5 ml)
  2. addition, the reaction mixture was diluted with EA
  3. washwashed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a crude product as a white solid
  8. customThe crude product was purified by silica gel column chromatography (eluent, EA:hexanes (4:1))

Sources & evidence

ORD record
ord-2f29399ea12741b591cc550038d5094f
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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