Water → Ethyl orotate

HRID 1671483Notes

Reaction equation

HRID 1671483 reaction equation
O.[C:2]([OH:12])(=[O:11])[C:3]1[NH:10][C:8](=[O:9])[NH:7][C:5](=[O:6])[CH:4]=1.N12CCCN=C1CCC[CH2:15][CH2:14]2.C(I)C.O>CN(C)C=O>[C:2]([O:12][CH2:14][CH3:15])(=[O:11])[C:3]1[NH:10][C:8](=[O:9])[NH:7][C:5](=[O:6])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 162185041,2,3,6-Tetrahydro-2,6-dioxo-4-pyrimidinecarboxylic acid monohydrate

Product 1

HCID 549450Ethyl orotateYield 87,400.602%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Orotic acid monohydrate (53.19 g, 0.306 mmol) was added to a solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (46.51 g, 0.306 mmol) in dimethylformamide (85 ml). After stirring for 5 min., ethyl iodide (57.14 g, 0.366 mmol) was added to the solution and the mixture was heated at 60° C. for 5 hrs. Water (1 L) was added, and the resulting precipitate was collected by filtration, washed with water, and dried to give ethyl orotate (49.25 g, 88%).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-192370183dd54a67b7d60c20efe49261
Source dataset
uspto-grants-2011_08
Patent number
US07994315B2

Reaction notes

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