Hydrochloric Acid → Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamate

HRID 1262794Notes

Reaction equation

HRID 1262794 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[H-].[Na+].[C:13](=O)([O:16]C)[O:14][CH3:15].Cl.[Na+].[Cl-]>C1COCC1>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:1][C:13](=[O:16])[O:14][CH3:15])[N:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 5872364-Methoxy-6-methylpyrimidin-2-amine

Product 1

HCID 13072161Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-4-methoxy-6-methylpyrimidine (50 g) was added portion wise to 50% sodium hydride (42.8 g) in 1 L dry THF. After stirring for 1/2 hour, dimethyl carbonate (58.5 g) was added dropwise with cooling. The mixture was stirred under nitrogen for ~16 hours at ambient temperature. Concentrated HCl (80 ml) was added slowly and using external cooling a pot temperature of ~25° C. was maintained. Saturated aqueous NaCl (80 ml) was then added. The solvents were decanted from the precipitated solids and dried over Na2SO4. Filtering and evaporating the solvents afforded the crude material which was recrystallized from hexane. 54 g m.p. 89°-92.5° C. The infrared spectrum showed characteristic absorption bonds at 3400 and 1760 cm-1.

Workup

  1. temperaturewith cooling
  2. stirringThe mixture was stirred under nitrogen for ~16 hours at ambient temperature
  3. temperatureusing external cooling a pot temperature of ~25° C.
  4. temperaturewas maintained
  5. customThe solvents were decanted from the precipitated solids
  6. dry with materialdried over Na2SO4
  7. filtrationFiltering
  8. customevaporating the solvents

Sources & evidence

ORD record
ord-66aca42329c14408a2eb9a66bb3e8f6e
Source dataset
uspto-grants-1984_06
Patent number
US04453970

Reaction notes

Loading…