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

HRID 426274Notes

Reaction equation

HRID 426274 reaction equation
[Br:1][C:2]1[C:3]([C:12]([C:14]2[CH:15]=[C:16]([CH:19]=[C:20]([CH3:22])[CH:21]=2)[C:17]#[N:18])=[O:13])=[N:4][C:5]([O:10]C)=[N:6][C:7]=1[O:8]C>C(Br)(=O)C>[Br:1][C:2]1[C:7](=[O:8])[NH:6][C:5](=[O:10])[NH:4][C:3]=1[C:12]([C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([CH3:22])[CH:21]=1)[C:17]#[N:18])=[O:13]

Participants

3

Reactant 1

HCID 591847973-(5-Bromo-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

Product 1

HCID 596868483-(5-Bromo-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 10482Acetyl bromideSolvent

Procedure

To a solution of 3-(5-bromo-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (0.158 g, 0.436 mmol) in acetyl bromide (2.0 mL) was heated at 65° C. for 24 h. Reaction mixture was concentrated and flash column chromatography (silica gel, 0 to 80% ethyl acetate/hexane) to give a yellow film (0.0802 g, 55%). 1H NMR (300 MHz, CD3OD): δ 8.18 (s, 1H), 8.09 (s, 1H), 7.90 (s, 1H), 2.46 (s, 3H). Mass spectrum: 335.3 (M+H)+.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. customflash column chromatography (silica gel, 0 to 80% ethyl acetate/hexane) to give a yellow film (0.0802 g, 55%)

Sources & evidence

ORD record
ord-78c89ff558f54aa480e5595429dd5a2a
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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