Hydrochloric Acid → Methyl (4,6-dimethoxypyrimidin-2-yl)carbamate

HRID 542681Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[H-].[Na+].[CH3:14][O:15][C:16](=O)[O:17]C.Cl.[Cl-].[Na+]>O1CCCC1>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH:1][C:16](=[O:17])[O:15][CH3:14])[N:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

2-Amino-4,6-dimethoxypyrimidine (56 g) was added portionwise to 50% sodium hydride (42.8 g) in 1000 ml of dry tetrahydrofuran. After stirring for 0.5 hour, dimethylcarbonate (58.5 g) was added dropwise with cooling. The mixture was stirred under nitrogen for about 16 hours at ambient temperature. Concentrated HCl (80 ml) was added slowly as external cooling was used to maintain a pot temperature of about 25° C. Saturated aqueous sodium chloride (80 ml) was then added. The solvents were decanted from the precipitated solids and dried over sodium sulfate. Filtration and evaporation of the solvents afforded the crude material which was recrystallized from hexane to yield 54 g of the title compound, m.p. 81°-83° C. The IR spectrum showed characteristic absorption bands at 3400 and 1760 cm-1.

Workup

temperaturewith cooling
stirringThe mixture was stirred under nitrogen for about 16 hours at ambient temperature
temperatureas external cooling
customThe solvents were decanted from the precipitated solids
dry with materialdried over sodium sulfate
filtrationFiltration and evaporation of the solvents
customafforded the crude material which
customwas recrystallized from hexane

Sources & evidence

ORD record: ord-51a4e96f40454b538c968ecb892cac72
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04659368

Reaction notes

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