Dimethyl Carbonate → HCID 22139127, compound

HRID 1920986Notes

Reaction equation

HRID 1920986 reaction equation
[C:1](=[O:6])(OC)OC.C[O-].[Na+].[NH2:10][C:11]1[C:16]([CH2:17][NH:18][CH3:19])=[CH:15][C:14]([Br:20])=[CH:13][N:12]=1>CO.O>[Br:20][C:14]1[CH:13]=[N:12][C:11]2[NH:10][C:1](=[O:6])[N:18]([CH3:19])[CH2:17][C:16]=2[CH:15]=1

Participants

6

Reactant 3

HCID 12021Dimethyl CarbonateHCID 10942334Sodium MethoxideHCID 221390775-Bromo-3-[(methylamino)methyl]pyridin-2-amine

Product 1

HCID 22139127HCID 22139127, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of dimethyl carbonate (2.14 g, 23.7 mmole) and sodium methoxide (1.0 mL, 4.5 mmole. 25% wt in CH3OH) in CH3OH (25 mL) was added 2-amino-5-bromo-3-(methylaminomethyl)pyridine (1.0 g, 4.62 mmole). The reaction was heated at 50° C. overnight, diluted with H2O (1 mL) and concentrated. Toluene was added to the reaction residue and the contents were heated to reflux for 12 hr under a Dean-Stark apparatus. The reaction was cooled to RT, diluted with EtOAc, and washed with H2O. Purification on Silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH) gave the title compound (0.75 g, 67%) as an off-white solid: MS (ES) m/e 243 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additionToluene was added to the reaction residue
  3. temperaturethe contents were heated
  4. temperatureto reflux for 12 hr under a Dean-Stark apparatus
  5. temperatureThe reaction was cooled to RT
  6. additiondiluted with EtOAc
  7. washwashed with H2O
  8. customPurification on Silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH)

Sources & evidence

ORD record
ord-6dfd1fd03abe4b8d84f7538be2675872
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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