3-(5-Dimethylamino-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile → 3-(5-Dimethylamino-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

HRID 426270Notes

Reaction equation

HRID 426270 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[C:4]([C:13]([C:15]2[CH:16]=[C:17]([CH:20]=[C:21]([CH3:23])[CH:22]=2)[C:18]#[N:19])=[O:14])=[N:5][C:6]([O:11]C)=[N:7][C:8]=1[O:9]C>C(Br)(=O)C>[CH3:1][N:2]([CH3:24])[C:3]1[C:8](=[O:9])[NH:7][C:6](=[O:11])[NH:5][C:4]=1[C:13]([C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([CH3:23])[CH:22]=1)[C:18]#[N:19])=[O:14]

Participants

3

Reactant 1

HCID 591847653-(5-Dimethylamino-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

Product 1

HCID 591846513-(5-Dimethylamino-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 10482Acetyl bromideSolvent

Procedure

A solution of 3-(5-dimethylamino-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (0.0834 g, 0.255 mmol) in acetyl bromide (3.0 mL) was heated at 70° C. for 12 h. Reaction mixture was concentrated and purified by reverse phase HPLC (Phenomenex Synergi® column, 5 to 100% acetonitrile/H2O) to give an orange solid after lyophilization (0.030 g, 39%). 1H NMR (300 MHz, CDCl3): δ 9.55 (br s, 1H), 9.32 (br s, 1H), 7.85 (s, 1H), 7.79 (s, 1H), 7.64 (s, 1H), 2.45 (s, 9H). Mass spectrum: 299.1 (M+H)+.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. custompurified by reverse phase HPLC (Phenomenex Synergi® column, 5 to 100% acetonitrile/H2O)
  4. customto give an orange solid after lyophilization (0.030 g, 39%)

Sources & evidence

ORD record
ord-0783336680c94d25b1da6aca294f5386
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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