2-(Methylamino)ethanol → 6-((2-hydroxyethyl)(methyl)amino)pyrimidine-2,4(1H,3H)-dione

HRID 873037Notes

Reaction equation

HRID 873037 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].Cl[C:7]1[NH:12][C:11](=[O:13])[NH:10][C:9](=[O:14])[CH:8]=1>[I-].[K+].O>[OH:5][CH2:4][CH2:3][N:2]([CH3:1])[C:7]1[NH:12][C:11](=[O:13])[NH:10][C:9](=[O:14])[CH:8]=1

Participants

5

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 732726-Chlorouracil

Product 1

HCID 867241596-((2-hydroxyethyl)(methyl)amino)pyrimidine-2,4(1H,3H)-dioneYield 75.1%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a microwave reaction tube 2-(methylamino)ethanol (1.652 g, 22 mmol), 6-chloropyrimidine-2,4(1H,3H)-dione (1.465 g, 10 mmol), potassium iodide (KI) (0.017 g, 0.1 mmol) and water (20 mL) were added. The mixture was heated to 120° C. by microwave (Biotage Initiator) and stirred for 2 h. Then the solution was concentrated in vacuo to remove all the water. EtOH (10 mL) was added to the resultant residue. The suspension was filtered and the filter cake was collected to afford the title compound as a light-yellow solid (1.390 g, 75% yield),

Workup

  1. additionwere added
  2. concentrationThen the solution was concentrated in vacuo
  3. customto remove all the water
  4. additionEtOH (10 mL) was added to the resultant residue
  5. filtrationThe suspension was filtered
  6. customthe filter cake was collected

Sources & evidence

ORD record
ord-db23b6ba5cb1450290b0431a9021b412
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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