Acetyl bromide → 3-(5-Cyclopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

HRID 426254Notes

Reaction equation

C(Br)(=O)C.[CH:5]1([C:8]2[C:9]([C:18]([C:20]3[CH:21]=[C:22]([CH:25]=[C:26]([CH3:28])[CH:27]=3)[C:23]#[N:24])=[O:19])=[N:10][C:11]([O:16]C)=[N:12][C:13]=2[O:14]C)[CH2:7][CH2:6]1>>[CH:5]1([C:8]2[C:13](=[O:14])[NH:12][C:11](=[O:16])[NH:10][C:9]=2[C:18]([C:20]2[CH:21]=[C:22]([CH:25]=[C:26]([CH3:28])[CH:27]=2)[C:23]#[N:24])=[O:19])[CH2:7][CH2:6]1

Participants

Reactant 2

HCID 10482Acetyl bromide

HCID 591847753-(5-Cyclopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile

Product 1

HCID 591847043-(5-Cyclopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrileYield 77.6%

Conditions

Temperature: 60 °C

Procedure

Acetyl bromide (1 mL, excess) was added to 3-(5-cyclopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (31 mg, 0.096 mmol). The reaction was heated to 60° C. for 1 hour. The reaction was concentrated down and purified (silica gel, 20-80% EtOAc/hexane) to give white solid (22 mg, 77%). LC-MS shows 294.0 (M−1). 1H NMR (300 MHz, CDCl3): δ 8.04 (s, 1H), 7.97 (s, 1H), 7.75 (s, 1H), 2.50 (s, 3H), 1.17 (m, 1H), 0.56 (m, 2H), 0.49 (m, 2H).

Workup

concentrationThe reaction was concentrated down
custompurified (silica gel, 20-80% EtOAc/hexane)

Sources & evidence

ORD record: ord-9a7f0f57f718489bb11c96aa07117722
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106064B2

Reaction notes

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