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

HRID 2278560Notes

Reaction equation

HRID 2278560 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, twice 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, twice 500 ml of water
  6. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-257ef5685ac94b4490e2bef9d35979f2
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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