Hydrochloric Acid → 2-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acid

HRID 2287620Notes

Reaction equation

HRID 2287620 reaction equation
[NH:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20]C)=[O:19].Cl>CN(C)C=O.O>[C:18]([CH2:17][N:1]1[CH:9]=[C:7]([CH3:8])[C:5](=[O:6])[NH:4][C:2]1=[O:3])([OH:20])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1135ThymineHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 8537532-(5-Methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of thymine (0.317 mole) and potassium carbonate (0.634 mole) in dimethylformamide (900 ml) is added methyl bromoacetate (0.634 mole) and the mixture is stirred vigorously overnight under nitrogen. The mixture is filtered, washed with ether and evaporated to dryness, in vacuo to afford a colorless solid. The solid residue is treated with water (300 ml) and 4 N hydrochloric acid (12 ml), stirred for 20 minutes at 0° C., filtered and washed with water (2×100 ml). The precipitate is treated with water and 2 N sodium hydroxide (60 ml), and is boiled for 10 minutes. The mixture is cooled at 0° C., filtered, and then pricipitated by the addition of 4 N hydrochloric acid (70 ml) to give the title compound.

Workup

  1. filtrationThe mixture is filtered
  2. washwashed with ether
  3. customevaporated to dryness, in vacuo
  4. customto afford a colorless solid
  5. stirringstirred for 20 minutes at 0° C.
  6. filtrationfiltered
  7. washwashed with water (2×100 ml)
  8. additionThe precipitate is treated with water and 2 N sodium hydroxide (60 ml)
  9. waitis boiled for 10 minutes
  10. filtrationfiltered
  11. additionpricipitated by the addition of 4 N hydrochloric acid (70 ml)

Sources & evidence

ORD record
ord-bd5bc0a6083a4832ad2b667d013d3a0e
Source dataset
uspto-grants-2000_07
Patent number
US06084082

Reaction notes

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