Ethanol → [4-(2-Ethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid ethyl ester

HRID 2278537Notes

Reaction equation

HRID 2278537 reaction equation
[CH2:1]([CH:3]1[O:8][CH2:7][CH2:6][NH:5][CH2:4]1)[CH3:2].C([N:12]([CH2:16][CH3:17])C(C)C)(C)C.Cl.C(O[C:22](=[NH:29])[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])C.[CH2:30]([OH:32])C>>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][C:22]1[NH:29][C:30](=[O:32])[CH:17]=[C:16]([N:5]2[CH2:6][CH2:7][O:8][CH:3]([CH2:1][CH3:2])[CH2:4]2)[N:12]=1)[CH3:28]

Participants

5

Reactant 4

HCID 702EthanolHCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideHCID 81531DiisopropylethylamineHCID 149332062-Ethylmorpholine

Product 1

HCID 136378675[4-(2-Ethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid ethyl ester

Conditions

Temperature
130 °C

Procedure

In a microwave tube, 0.45 g of 2-ethylmorpholine is placed in 10 ml of ethanol, 2.11 ml of N,N-diisopropylethylamine and 2.29 g of ethyl 3-ethoxy-3-iminopropanoate hydrochloride. The tube is then microwave-heated at 130° C. for 1 hour and then allowed to return to ambient temperature. The reaction mixture is concentrated under reduced pressure. After purification by silica column chromatography, eluent: 90/05 dichloromethane/methanol, 550 mg of [4-(2-ethylmorpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetic acid ethyl ester are obtained in the form of a beige powder, the characteristics of which are the following:

Workup

  1. customto return to ambient temperature
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customAfter purification by silica column chromatography, eluent

Sources & evidence

ORD record
ord-66c32ae1e2cd4563b92bbcebf93c335a
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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