Sodium Methoxide → HCID 19106906, compound

HRID 248615Notes

Reaction equation

HRID 248615 reaction equation
C[O-].[Na+].[C:4]([N:6]=[C:7]([NH:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH2:8][CH2:9][CH3:10])#[N:5]>CO>[NH2:5][C:4]1[N:6]=[C:7]([CH2:8][CH2:9][CH3:10])[NH:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178449215HCID 178449215, compound

Product 1

HCID 19106906HCID 19106906, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
13 °C

Procedure

To stirred methanol at -2° C. was added sodium methoxide (108 g, 2.0 mol) in portions over a period of 40 minutes. To this clear solution at -3° C. was added a solution of methyl N-(N'-cyanobutyrimidoyl)glycinate (Example 3, 344 g, 1.9 mol) in methanol (600 mL) over a period of 30 minutes. The resulting orange solution was allowed to warm to 13° C. over a period of 1 hour, then refluxed for 1 hour. The dark solution was cooled to room temperature and evaporated to dryness under reduced pressure. The residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate (4×1 L) and the combined organic layers washed with a saturated aqueous solution of sodium chloride. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and the filtrate evaporated to dryness under reduced pressure. The residue was recrystallized from ethyl acetate at -10° C. to afford 131 g (38% yield) of methyl 4-amino-2-propylimidazol-5-carboxylate, mp 133°-136° C. MS (DEI) 184 (M+1).

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureThe dark solution was cooled to room temperature
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was partitioned between water and ethyl acetate
  5. extractionThe aqueous layer was extracted with ethyl acetate (4×1 L)
  6. washthe combined organic layers washed with a saturated aqueous solution of sodium chloride
  7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate evaporated to dryness under reduced pressure
  10. customThe residue was recrystallized from ethyl acetate at -10° C.

Sources & evidence

ORD record
ord-819e67398d7f4731ad15b443f0c90abf
Source dataset
uspto-grants-1993_05
Patent number
US05210211

Reaction notes

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