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

HRID 1981270Notes

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+].[CH3:13][O:14][C:15](=O)[O:16]C.Cl>O1CCCC1>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:1][C:15](=[O:16])[O:14][CH3:13])[N:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of 50 g of 2-amino-4-methoxy-6-methylpyrimidine in 1000 ml of tetrahydrofuran was added portionwise, under a nitrogen atmosphere, 42.8 g of 50% sodium hydride while cooling the reaction flask in an ice-water bath. After stirring one hour at 25° C., 58.5 g of dimethylcarbonate was added dropwise at 5° to 25° C. The suspension was stirred about 16 hours at ambient temperature, then 80 ml of concentrated hydrochloric acid was added dropwise while maintaining a reaction temperature of 20° to 25° C. with external ice-bath cooling. The suspension was stirred 0.5 hour, filtered, and the filtrate was dried over sodium sulfate and then concentrated in vacuo. The residue was recrystallized from hexane to yield 54 g of the title compound, m.p. 89°-92.5° C.

Workup

additionwas added portionwise, under a nitrogen atmosphere
stirringThe suspension was stirred about 16 hours at ambient temperature
temperaturewhile maintaining a reaction temperature of 20° to 25° C. with external ice-bath
temperaturecooling
stirringThe suspension was stirred 0.5 hour
filtrationfiltered
dry with materialthe filtrate was dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was recrystallized from hexane

Sources & evidence

ORD record: ord-3d53bf2d292c49a0a00f321034dc506e
Source dataset: uspto-grants-1985_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04514211

Reaction notes

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