Methyl iodide → Ethyl [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate

HRID 880120Notes

Reaction equation

[N:1]1([C:7]2[N:8]=[C:9]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:10][C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:20](=O)([O-])[O-].[K+].[K+].CI>O1CCOCC1>[CH3:20][N:10]1[C:11](=[O:13])[CH:12]=[C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[N:8]=[C:9]1[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

Conditions

Temperature: 40 °C

Procedure

Added to a solution of 500 mg of ethyl [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate prepared in stage 1 of Example 1 in 1.5 ml of dioxane, are 330 mg of potassium carbonate and 150 ml of methyl iodide. The reaction mixture is heated at 40° C. for 16 minutes, and then cooled to ambient temperature. The suspension is filtered through sintered glass and then rinsed with dioxane and the filtrate is concentrated under reduced pressure. The residue is purified by silica column chromatography, elution being carried out with a mixture of dichloromethane, acetonitrile and methanol (980101, 960202, then 900505 VNN). 200 mg of ethyl [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate are obtained in the form of a white solid, the characteristics of which are the following:

Workup

temperaturecooled to ambient temperature
filtrationThe suspension is filtered through sintered glass
washrinsed with dioxane
concentrationthe filtrate is concentrated under reduced pressure
customThe residue is purified by silica column chromatography, elution
additionbeing carried out with a mixture of dichloromethane, acetonitrile and methanol (980101, 960202

Sources & evidence

ORD record: ord-32812b4fb10e42a8902c40b31bb16525
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993565B2

Reaction notes

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