Dimethylformamide → 6-amino-5-formyl-3-methyl-1-phenyl-2,4 (1H, 3H)-pyrimidinedione

HRID 1417710Notes

Reaction equation

HRID 1417710 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[N:5]([CH3:15])[C:4](=[O:16])[CH:3]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN(C)[CH:26]=[O:27]>O>[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[N:5]([CH3:15])[C:4](=[O:16])[C:3]=1[CH:26]=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 16492566-Amino-3-methyl-1-phenylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 131340586-amino-5-formyl-3-methyl-1-phenyl-2,4 (1H, 3H)-pyrimidinedioneYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Amino-3-methyl-1-phenyl-2,4 (1H, 3H)-pyrimidinedione (5.00 g, 23 mmol) was suspended in dimethylformamide (77 mL). To the resultant suspension was added phosphorus oxychloride (2.57 mL, 27.6 mmol), and the resultant mixture was reacted at 60° C. for 3 h. The reaction mixture was diluted with water, and adjusted to ca. pH 12 with sodium hydroxide. The precipitates formed in the reaction mixture was filtered to give a crude product. The crude product was recrystallized from a mixture of ethanol, ethyl acetate and water to give an aldehyde, 6-amino-5-formyl-3-methyl-1-phenyl-2,4 (1H, 3H)-pyrimidinedione (yield 75%).

Workup

  1. customThe precipitates formed in the reaction mixture
  2. filtrationwas filtered
  3. customto give a crude product
  4. customThe crude product was recrystallized from a mixture of ethanol, ethyl acetate and water

Sources & evidence

ORD record
ord-4beba64bf2244ce6b9ff5a9810fe865a
Source dataset
uspto-grants-1999_03
Patent number
US05877318

Reaction notes

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