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

HRID 2309326Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:11])[N:3]=1.[H-].[Na+].[CH3:14][O:15][C:16](=O)[O:17]C.Cl>O1CCCC1>[CH3:14][O:15][C:16](=[O:17])[NH:1][C:2]1[N:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:11])[N:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of 53.7 g of 2-amino-4-cyclopropyl-6-methylpyrimidine in 1000 ml of tetrahydrofuran is 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 is added dropwise at 5° to 25°. The suspension is stirred about 16 hours at ambient temperatures, then 80 ml of concentrated hydrochloride acid is added dropwise under a nitrogen atmosphere while maintaining a reaction temperature of 20° to 25° with external ice-bath cooling. The suspension is stirred 0.5 hour, filtered, and the filtrate is dried over sodium sulfate and concentrated in vacuo to give the subject compound.

Workup

additionis added portionwise, under a nitrogen atmosphere
stirringThe suspension is stirred about 16 hours at ambient temperatures
temperaturewhile maintaining a reaction temperature of 20° to 25° with external ice-bath
temperaturecooling
stirringThe suspension is stirred 0.5 hour
filtrationfiltered
dry with materialthe filtrate is dried over sodium sulfate
concentrationconcentrated in vacuo
customto give the subject compound

Sources & evidence

ORD record: ord-42e4bcbcc688461f9567492c8eee3d04
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04695310

Reaction notes

Loading…