1,1-Dimethoxyethyl(dimethyl)amine → HCID 67172220, compound

HRID 1891275Notes

Reaction equation

HRID 1891275 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[CH2:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[N:6][CH:7]=1.[CH3:16]OC(OC)(N(C)C)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[CH2:13][C:12](=[O:14])[N:11]([CH3:16])[C:10]2=[O:15])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 67173009HCID 67173009, compound

Product 1

HCID 67172220HCID 67172220, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

1-((5-bromopyridin-2-yl)methyl)imidazolidine-2,4-dione (9J3) (0.926 mmol, 250 mg) was mixed with toluene (2.5 ml) and N,N-dimethylacetamide dimethyl acetal (9J4) (3.70 mmol, 490 mg) and heated in the microwave at 150° C. for 15 minutes. The volatile components were removed under high vacuum and the resulting oil purified on silica eluting with 0-100% ethyl acetate/heptane to afford 1-((5-bromopyridin-2-yl)methyl)-3-methylimidazolidine-2,4-dione (9J5) 220 mg (84%); 1H NMR (400 MHz, CDCl3) 8.62 (d, 1H) 7.81 (dd, 1H) 7.20 (d, 1H) 4.63 (s, 2H) 3.98 (s, 2H) 3.05 (s, 3H).

Workup

  1. customThe volatile components were removed under high vacuum
  2. customthe resulting oil purified on silica eluting with 0-100% ethyl acetate/heptane

Sources & evidence

ORD record
ord-87886334197845de80c29fc489c058d5
Source dataset
uspto-grants-2013_08
Patent number
US08507521B2

Reaction notes

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