Methanol → HCID 178481362, compound

HRID 1111425Notes

Reaction equation

HRID 1111425 reaction equation
O.[NH2:2][C:3]1[C:4](=[O:13])[N:5]([CH3:12])[C:6](=[O:11])[N:7]([CH3:10])[C:8]=1[NH2:9].[CH:14]([C:16]1[CH:26]=[CH:25][C:19]([CH:20]=[CH:21][C:22]([OH:24])=[O:23])=[CH:18][CH:17]=1)=O.CO.NC1N(C)C(=O)N(C)C(=O)C=1CC(=CC1C=CC=CC=1)C(O)=O>C(O)(=O)C.[N+](C1C=CC=CC=1)([O-])=O>[CH3:12][N:5]1[C:4](=[O:13])[C:3]2[N:2]=[C:14]([C:16]3[CH:26]=[CH:25][C:19](/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23])=[CH:18][CH:17]=3)[NH:9][C:8]=2[N:7]([CH3:10])[C:6]1=[O:11]

Participants

7

Reactant 4

HCID 887MethanolHCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 122574835,6-diamino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione hydrateHCID 86744444(6-Amino-1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxo-5-pyrimidinylmethyl]cinnamic acid

Product 1

HCID 178481362HCID 178481362, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7416NitrobenzeneSolvent

Procedure

5,6-Diamino-l,3-dimethyluracil hydrate (1.70 g, 10.0 mmol) and 4-formylcinnamic acid (1.76 g, 10.0 mmol) were refluxed in acetic acid (10 mL)-methanol (100 mL) for 0.5 hour. (E)-4[(6-Amino-l,2,3-4-tetrahydro-1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)iminomethyl]cinnamic acid was precipitated as a yellow powder (1.84 g, 56%); mp 299°-301° C. with effervescence. Analysis for (C16H16N4O4): C,58.53;H,491;N,1707. Found: C,58.36;H,4.93;N,16.90. The structure was confirmed by H-NMR and EI mass spectrum. The (E)-4-[(6-amino-1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxo-5-pyrimidinylmethyl]cinnamic acid (500 mg, 1.52 mmol) was then refluxed in nitrobenzene (125 mL) for 2.5 hours with slow distillation to remove water formed. The reaction mixture was cooled and the precipitate washed with ether. Recrystallization from N,N-dimethylformamide-water gave the monohydrate of the title compound as a pale yellow powder; mp>380° C. Analysis for (C16H14N4O4H2O):C, 55.81; H, 4.68; N, 16.27. Found: C, 56.05: H, 4.69; N, 16.27. The structure was confirmed by 1H-NMR and EI mass spectrum.

Workup

  1. custom(E)-4[(6-Amino-l,2,3-4-tetrahydro-1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)iminomethyl]cinnamic acid was precipitated as a yellow powder (1.84 g, 56%)
  2. customto remove water
  3. customformed
  4. temperatureThe reaction mixture was cooled
  5. washthe precipitate washed with ether
  6. customRecrystallization from N,N-dimethylformamide-water

Sources & evidence

ORD record
ord-80d90501ba4f4df294038bc7a8a03896
Source dataset
uspto-grants-1990_12
Patent number
US04980379

Reaction notes

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