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

HRID 2278483Notes

Reaction equation

HRID 2278483 reaction equation
Cl.C(O[C:5](=[NH:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])C.C([N:16]([CH2:20][CH3:21])C(C)C)(C)C.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[CH2:28]([OH:30])C>>[N:22]1([C:20]2[N:16]=[C:5]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[NH:12][C:28](=[O:30])[CH:21]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 8083MorpholineHCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideHCID 81531Diisopropylethylamine

Product 1

HCID 135905419Ethyl 2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate

Conditions

Temperature
95 °C

Procedure

168.5 ml of ethyl 3-ethoxy-3-iminopropanoate hydrochloride and then 155 ml of N,N-diisopropylethylamine in 200 ml of ethanol are added to a solution of 25 g of morpholine in 400 ml of ethanol, heated to 95° C. The reaction mixture is heated at 95° C. for 30 hours and then allowed to return to ambient temperature. The precipitate formed is filtered off through sintered glass and then washed with 100 ml of ethanol, 2 times 500 ml of water and, finally, 500 ml of ethyl ether. The solid is dried under vacuum so as to give 35 g of ethyl [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate in the form of a white solid, the characteristics of which are the following:

Workup

  1. temperatureThe reaction mixture is heated at 95° C. for 30 hours
  2. customto return to ambient temperature
  3. customThe precipitate formed
  4. filtrationis filtered off through sintered glass
  5. washwashed with 100 ml of ethanol, 2 times 500 ml of water
  6. customThe solid is dried under vacuum so as

Sources & evidence

ORD record
ord-8cf2c53a880e427b9f7daaff610e06de
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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