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

HRID 2278612Notes

Reaction equation

[C:1](=O)([O-])[O-].[K+].[K+].CI.[N:9]1([C:15]2[N:16]=[C:17]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[NH:18][C:19](=[O:21])[CH:20]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1>O1CCOCC1>[CH3:1][N:18]1[C:19](=[O:21])[CH:20]=[C:15]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[N:16]=[C:17]1[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

Conditions

Temperature: 40 °C

Procedure

330 mg of potassium carbonate and 0.15 ml of methyl iodide are added to a solution of 500 mg of ethyl [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (prepared in step 1d of example 1d) in 1.5 ml of dioxane. The reaction mixture is heated at 40° C. for 16 hours 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 chromatography on a silica column, elution being carried out with a mixture of dichloromethane, acetonitrile and methanol (98/01/01, 96/02/02, then 90/05/05 V/V/V). 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 chromatography on a silica column, elution
additionbeing carried out with a mixture of dichloromethane, acetonitrile and methanol (98/01/01, 96/02/02

Sources & evidence

ORD record: ord-0b9ffca1f20947e6a9b85d1815e8e1f6
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133168B2

Reaction notes

Loading…