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

HRID 2278563ノート

反応式

HRID 2278563 の反応式
[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]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135905419Ethyl 2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate

生成物 1

HCID 57523683Ethyl [1-methyl-4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate収率 38%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
40 °C

実験手順

330 mg of potassium carbonate and 150 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 1c of example 1c) in 1.5 ml of dioxane. The reaction mixture is heated at 40° C. for 16 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 (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:

後処理

  1. temperaturecooled to ambient temperature
  2. filtrationThe suspension is filtered through sintered glass
  3. washrinsed with dioxane
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is purified by silica column chromatography, elution
  6. additionbeing carried out with a mixture of dichloromethane, acetonitrile and methanol (98/01/01, 96/02/02

出典と根拠

ORDレコード
ord-2609287d2b4641c4868221956ed2784c
出典データセット
uspto-grants-2015_09
特許番号
US09133168B2

反応ノート

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