4-Methylmorpholine → N-(2,4,6-Trioxo-5-phenyl-hexahydro-pyrimidin-5-yl)-malonamic acid methyl ester

HRID 1066061Notes

Reaction equation

HRID 1066061 reaction equation
[NH2:1][C:2]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7](=[O:8])[NH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10].CN1CCOCC1.[Cl-].[CH3:25][O:26][C:27](=[O:32])[CH2:28][C:29](O)=[O:30]>C(#N)C>[CH3:25][O:26][C:27](=[O:32])[CH2:28][C:29]([NH:1][C:2]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3](=[O:10])[NH:4][C:5](=[O:9])[NH:6][C:7]1=[O:8])=[O:30]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 158573525-Amino-5-phenyl-2,4,6-trioxopyrimidineHCID 86615040Malonic acid methylester chloride

Product 1

HCID 15857349N-(2,4,6-Trioxo-5-phenyl-hexahydro-pyrimidin-5-yl)-malonamic acid methyl esterYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2 g 5-amino-5-phenyl-2,4,6-trioxopyrimidine is dissolved in 20 ml acetonitrile and admixed with 1.5 ml N-methyl-morpholine. 1.03 ml malonic acid monomethyl ester chloride is added dropwise while stirring and cooling on ice and the suspension is stirred for 2 hours at room temperature. The precipitate is suction filtered, washed with acetonitrile, water and again with acetonitrile and dried. 1.97 g (68%) of the title compound is obtained.

Workup

  1. temperaturecooling on ice
  2. stirringthe suspension is stirred for 2 hours at room temperature
  3. filtrationfiltered
  4. washwashed with acetonitrile, water and again with acetonitrile
  5. customdried

Sources & evidence

ORD record
ord-5f40376ed5e945c8a93e44a12aeb39ab
Source dataset
uspto-grants-2001_06
Patent number
US06242455B1

Reaction notes

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