Methyl iodide → 1-(6-Bromo-pyridin-3-yl)-3,4,4-trimethyl-imidazolidin-2-one

HRID 868812Notes

Reaction equation

[Br:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][C:11]([CH3:14])([CH3:13])[NH:10][C:9]2=[O:15])=[CH:4][CH:3]=1.IC.[H-].[Na+].[C:20]([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][C:11]([CH3:13])([CH3:14])[N:10]([CH3:20])[C:9]2=[O:15])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 2.5 °C

Procedure

(810 mg, 3.0 mmol) 1-(6-Bromo-pyridin-3-yl)-4,4-dimethyl-imidazolidin-2-one (Example 3, step 1) was dissolved in DMF (8 ml) and cooled to 0-5° C. Iodomethane (640 mg, 280 μl, 4.5 mmol, 1.5 equiv.) and NaH (60%) (156 mg, 3.9 mmol, 1.3 equiv.) were added and the mixture was stirred for 2 hours at 0-5° C. The reaction mixture was treated with sat. NaHCO3 solution and extracted two times with EtOAc. The organic layers were extracted with water and brine, dried over Na2 SO4 and evaporated to dryness. The crude product was purified by flash chromatography on a silica gel column eluting with a heptane:ethyl acetate gradient 100:0 to 0:100. The desired 1-(6-bromo-pyridin-3-yl)-3,4,4-trimethyl-imidazolidin-2-one (800 mg, 94% yield) was obtained as a yellow solid, MS: m/e=284.1/286.0 (M+M+).

Workup

extractionextracted two times with EtOAc
extractionThe organic layers were extracted with water and brine
customdried over Na2 SO4
customevaporated to dryness
customThe crude product was purified by flash chromatography on a silica gel column
washeluting with a heptane

Sources & evidence

ORD record: ord-53eca3b05d084bce96f4699fa991040c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969338B2

Reaction notes

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