Acetic acid, 2-(4-formylphenoxy)- → Pyrimidin-2,4-dione, 6-amino-5-[(4-carboxymethoxy)benzimidoyl]-1,3-dipr

HRID 2309704Notes

Reaction equation

HRID 2309704 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)([OH:3])=[O:2].[NH2:14][C:15]1[C:16](=[O:29])[N:17]([CH2:26][CH2:27][CH3:28])[C:18](=[O:25])[N:19]([CH2:22][CH2:23][CH3:24])[C:20]=1[NH2:21]>CO.C(O)(=O)C>[NH2:21][C:20]1[N:19]([CH2:22][CH2:23][CH3:24])[C:18](=[O:25])[N:17]([CH2:26][CH2:27][CH3:28])[C:16](=[O:29])[C:15]=1[N:14]=[CH:10][C:9]1[CH:12]=[CH:13][C:6]([O:5][CH2:4][C:1]([OH:3])=[O:2])=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 89177Acetic acid, 2-(4-formylphenoxy)-HCID 50986055,6-Diamino-1,3-dipropyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 614654Pyrimidin-2,4-dione, 6-amino-5-[(4-carboxymethoxy)benzimidoyl]-1,3-dipr

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A representative synthesis of benzylidene adduct is given. Compound A (1.51 g, 8.37 mmol) was dissolved in a mixture of methanol (35 ml) and acetic acid (5 ml) in a 50 ml boiling flask on a steam bath. To this was added a methanolic solution (60 ml) of freshly synthesized 5,6-diamino-1,3-dipropyluracil. After heating 15 minutes, the volume was reduced by evaporation until crystallization occurred. Ether (40 ml) was added and the nearly white solid was collected. Yield 2.80 g (86%), mp 179°-180° C. Analysis (C19H24N4O5): calc. 58.60% C, 6.21% H, 14.39% N; found 58.72% C, 6.16% H, 14.43% N.

Workup

  1. customA representative synthesis of benzylidene adduct
  2. temperatureAfter heating 15 minutes
  3. customthe volume was reduced by evaporation until crystallization
  4. additionEther (40 ml) was added
  5. customthe nearly white solid was collected

Sources & evidence

ORD record
ord-1af5a30a224245769645271e64da0b4c
Source dataset
uspto-grants-1987_09
Patent number
US04696932

Reaction notes

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