5-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-isophthalonitrile → 5-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-isophthalonitrile

HRID 426280Notes

Reaction equation

HRID 426280 reaction equation
[CH:1]([C:4]1[C:5]([C:14]([C:16]2[CH:17]=[C:18]([C:24]#[N:25])[CH:19]=[C:20]([CH:23]=2)[C:21]#[N:22])=[O:15])=[N:6][C:7]([O:12]C)=[N:8][C:9]=1[O:10]C)([CH3:3])[CH3:2]>C(Br)(=O)C>[CH:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:12])[NH:6][C:5]=1[C:14]([C:16]1[CH:17]=[C:18]([C:24]#[N:25])[CH:19]=[C:20]([CH:23]=1)[C:21]#[N:22])=[O:15])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 591847555-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-isophthalonitrile

Product 1

HCID 591846985-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-isophthalonitrile

Reagents, catalysts & solvents 1

HCID 10482Acetyl bromideSolvent

Procedure

A solution of 5-(5-isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-isophthalonitrile (0.018 g, 0.0535 mmol) in acetyl bromide (0.7 mL) was heated at 60° C. for 5 h. Reaction mixture was concentrated and purified by flash column chromatography (silica gel, 0 to 5% methanol/dichloromethane) to give a yellow film (0.017 g, 97%). 1H NMR (300 MHz, CD3OD): δ 8.65 (s, 2H), 8.52 (s, 1H), 2.5-2.3 (m, 1H), 1.14 (s, 3H), 1.10 (s, 3H). Mass spectrum: 307.1 (M+H)+.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. custompurified by flash column chromatography (silica gel, 0 to 5% methanol/dichloromethane)
  4. customto give a yellow film (0.017 g, 97%)

Sources & evidence

ORD record
ord-14484ba0212f42f4b8289296abbd332c
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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