2,6-Dimethoxybenzoic Acid → 5-(4-Amino-3,5-dimethoxybenzyl)-2,4-(1H,3H)-pyrimidinedione

HRID 1589248Notes

Reaction equation

HRID 1589248 reaction equation
Cl.CN([CH2:5][C:6]1[C:7](=[O:13])[NH:8][C:9](=[O:12])[NH:10][CH:11]=1)C.[CH3:14][O:15][C:16]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[C:17]=1[NH2:18].COC1C=CC=C(OC)C=1C(O)=O>C(O)CO>[NH2:18][C:17]1[C:19]([O:23][CH3:24])=[CH:20][C:21]([CH2:5][C:6]2[C:7](=[O:13])[NH:8][C:9](=[O:12])[NH:10][CH:11]=2)=[CH:22][C:16]=1[O:15][CH3:14]

Participants

5

Reactant 3

HCID 151092,6-Dimethoxybenzoic AcidHCID 95940Benzenamine, 2,6-dimethoxy-HCID 122674355-Dimethylaminomethyluracil Hydrochloride

Product 1

HCID 136090865-(4-Amino-3,5-dimethoxybenzyl)-2,4-(1H,3H)-pyrimidinedioneYield 29%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 10.04 g (49 mmol) of 5-[(dimethylamino)methyl]uracil hydrochloride (B. Roth, J. Z. Strelitz, and B. S. Rauckman, J. Med. Chem. 23, 379 (1980) and 7.48 g (49 mmol) of 2,6-dimethoxyaniline (m.p. 73°-74.5°; prepared from 2,6-dimethoxybenzoic acid by the procedure in Org. Reactions 3, 330 (1946)) in 50 mL of ethylene glycol under nitrogen was heated at 145° for 5 hours. The mixture was cooled and the precipitated solid was collected, suspended in 300 mL of boiling ethanol and collected to give 3.91 g (29%) of the title compound; m.p. 243°-245° (dec.).

Workup

  1. temperatureThe mixture was cooled
  2. customthe precipitated solid was collected
  3. customcollected

Sources & evidence

ORD record
ord-c76c64ab73cb42db87859dc52a30cd66
Source dataset
uspto-grants-1986_02
Patent number
US04568744

Reaction notes

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