Acetic Acid → Methyl 5-(2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-7-yl)-2-methoxybenzoate

HRID 218352Notes

Reaction equation

HRID 218352 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[NH:5][C:4](=[O:9])[CH:3]=1.C(O)(=O)C.O.CN(C)/[CH:17]=[CH:18]/[C:19]([C:21]1[CH:22]=[CH:23][C:24]([O:31][CH3:32])=[C:25]([CH:30]=1)[C:26]([O:28][CH3:29])=[O:27])=O>CS(C)=O>[O:8]=[C:6]1[NH:7][C:2]2[N:1]=[C:19]([C:21]3[CH:22]=[CH:23][C:24]([O:31][CH3:32])=[C:25]([CH:30]=3)[C:26]([O:28][CH3:29])=[O:27])[CH:18]=[CH:17][C:3]=2[C:4](=[O:9])[NH:5]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 701206-AminouracilHCID 58015477Methyl 5-[(2E)-3-(dimethylamino)prop-2-enoyl]-2-methoxybenzoate

Product 1

HCID 44554230Methyl 5-(2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-7-yl)-2-methoxybenzoateYield 106.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
99 °C

Procedure

6-Aminouracil (14.32 g, 112.7 mmol) was added to glacial acetic acid (112.5 mL) and water (75 mL) and the mixture heated to 99° C. A solution of methyl 5-[(2E)-3-(dimethylamino)prop-2-enoyl]-2-methoxybenzoate (15 g, 56.3 mmol) in DMSO (75 mL) was then added over 180 minutes. The reaction was stirred at 99° C. for a further 90 minutes and cooled to 60° C. Water (75 mL) was then added and the reaction maintained at 60° C. for a further 60 minutes and then filtered off to afford a beige solid. The solid was washed with fresh water (75 mL) and dried visibly dry thus affording 19.6 g of water wet solid (9).

Workup

  1. temperaturecooled to 60° C
  2. temperaturethe reaction maintained at 60° C. for a further 60 minutes
  3. filtrationfiltered off
  4. customto afford a beige solid
  5. washThe solid was washed with fresh water (75 mL)
  6. customdried visibly
  7. customdry thus

Sources & evidence

ORD record
ord-0869baee4dd54e2eae5862a45b937885
Source dataset
uspto-grants-2012_06
Patent number
US08198441B2

Reaction notes

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