Acetic Acid → HCID 14257882, compound

HRID 2231772Notes

Reaction equation

HRID 2231772 reaction equation
O.[CH3:2][N:3]1[C:10]([NH2:11])=[C:9]([NH2:12])[C:7](=[O:8])[N:6]([CH3:13])[C:4]1=[O:5].[C:14]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)#[N:15].C(O)(=O)C>C(O)C>[OH2:5].[CH3:13][N:6]1[C:7](=[O:8])[C:9]2[NH:12][C:20]([C:19]3[CH:22]=[CH:23][C:16]([C:14]#[N:15])=[CH:17][CH:18]=3)=[N:11][C:10]=2[N:3]([CH3:2])[C:4]1=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 660424-CyanobenzaldehydeHCID 122574835,6-diamino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione hydrate

Product 1

HCID 14257882HCID 14257882, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

1,3-Dimethyl-8-(4-cyanophenyl)xanthine hydrate was prepared by treatment of 1,3-dimethyl-5,6-diaminouracil hydrate (9.0 g, 52.9 mmol) with 4-cyanobenzaldehyde (6.9 g, 52.7 mmol) in ethanol (700 ml) in the presence of acetic acid (3 ml) at reflux for 5 hours. The reaction mixture was cooled to 0° C. and the resulting precipitate was collected. The crude iminouracil was dissolved in ethylene glycol dimethyl ether (700 ml) and treated with DEAD (11 ml) at reflux for 4 hours. The reaction mixture was cooled to 0° C. and the resulting precipitate was collected and recrystallized from 4:4:2 methanol:ethyl acetate:water. mp.>300° C. IR (KBr) 3412, 3320, 2965, 2936, 2877, 1680, 1604, 1512 cm-1. Anal. Calcd. for C14H11N5O2.H2O. C,56.18, H, 4.37; N, 23.40. Found: C, 56.20; H, 4.04; N,23.17.

Workup

  1. temperatureat reflux for 5 hours
  2. customthe resulting precipitate was collected
  3. dissolutionThe crude iminouracil was dissolved in ethylene glycol dimethyl ether (700 ml)
  4. additiontreated with DEAD (11 ml)
  5. temperatureat reflux for 4 hours
  6. temperatureThe reaction mixture was cooled to 0° C.
  7. customthe resulting precipitate was collected
  8. customrecrystallized from 4:4:2 methanol

Sources & evidence

ORD record
ord-2bbab3eea860433fbdde5a3c7609c4a8
Source dataset
uspto-grants-1988_11
Patent number
US04783530

Reaction notes

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