Methyl iodide → HCID 118874970, compound

HRID 60153Notes

Reaction equation

HRID 60153 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([NH:11][C:12]([NH:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[O:13])=[CH:9][N:10]=1)[C:5]([OH:7])=O.[C:21]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[N:10]=[CH:9][C:8]2[N:11]([CH3:21])[C:12](=[O:13])[N:14]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:5](=[O:7])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1188749792-Chloro-5-(3-(3-methoxy-3-oxopropyl)ureido)isonicotinic acid

Product 1

HCID 118874970HCID 118874970, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-chloro-5-(3-(3-methoxy-3-oxopropyl)ureido)isonicotinic acid (33.8 g, 112 mmol) in acetone (386 mL) was added K2CO3 (46.4 g, 336 mmol) followed by CH3I (95.4 g, 672 mmol). The reaction was heated in a sealed tube at 40° C. for 24 h, cooled to RT, concentrated then diluted with EA (200 mL) and water (100 mL). The organic layer was washed with brine (100 mL), dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (10:1 to 2:1) to give methyl 3-(6-chloro-1-methyl-2,4-dioxo-1,2-dihydropyrido[3,4-d]pyrimidin-3(4H)-yl)propanoate (1.6 g, 11% yield) as a yellow solid. LCMS: MH+ 298 and TR=2.857 min.

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated
  3. additionthen diluted with EA (200 mL) and water (100 mL)
  4. washThe organic layer was washed with brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to a residue which
  7. customwas purified by chromatography
  8. washeluted with PE/EA (10:1 to 2:1)

Sources & evidence

ORD record
ord-4ad58cd356684c85a8205e647279563e
Source dataset
uspto-grants-2016_09
Patent number
US09440973B2

Reaction notes

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