Acetic Acid → 2,4(1H,3H)-Pyrimidinedione, 6-amino-1-methyl-5-nitroso-3-propyl-

HRID 1638328Notes

Reaction equation

HRID 1638328 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH2:10][CH2:11][CH3:12])[C:4](=[O:13])[CH:3]=1.[N:14]([O-])=[O:15].[Na+].C(O)(=O)C>C(O)C.O>[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH2:10][CH2:11][CH3:12])[C:4](=[O:13])[C:3]=1[N:14]=[O:15]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 116087Uracil, 6-amino-1-methyl-3-propyl-HCID 23668193Sodium Nitrite

Product 1

HCID 108461962,4(1H,3H)-Pyrimidinedione, 6-amino-1-methyl-5-nitroso-3-propyl-Yield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

6-Amino-1-methyl-3-propyl-2,4(1H,3H)pyrimidinedione (V. Papesch and E. F. Schroeder, J.Org.Chem. 1951, 16, 1879) (5.53 g, 27.5 mmol) was dissolved in hot 95% ethanol (20 ml)-water (120 ml). Sodium nitrite (2.32 g) and glacial acetic acid (2.4 ml) were added. The resulting mixture was allowed to cool to room temperature. Orange-pink crystals were filtered off and dried at 50° C. under vacuum to give purple crystals of 6-amino-1-methyl-5-nitroso-3-propyl-2,4 (1H,3H)-pyrimidinedione (2.92 g, 80%); mp 250° dec. Analysis for (C8H12N4O3): C,45.28; H,5.70; N,26.40. Found: C,45.12; H,5.74; N,26.34. 5,6-Diamino-1-methyl-3-propyl-2,4(1H,3H)pyrimidinedione was prepared freshly from 6-amino-1-methyl-5-nitroso-3-propyl-2,4(1H,3H)pyrimidinedione by ammonium sulfide reduction using the method of V. Papesch, M. Grove, and E. F. Schroeder (U.S. Pat. No. 2 602 795). This diamine (2.00 g, 10.0 mmol) was condensed with 4-formylcinnamic acid (1.76 g, 10.0 mmol) by the procedure of Example 2 to give the title compound as an ivory powder, after crystallization from N,N-dimethylformamide-water; mp>300° C. Analysis for (C18H18N4O4.1/5 DMF): C,60.54; H,5.30; N,15.94. Found: C,60.52; H,5.22; N,16.03.

Workup

  1. filtrationOrange-pink crystals were filtered off
  2. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-dbb591c554f0447fb1a85c6f6d9b4606
Source dataset
uspto-grants-1989_11
Patent number
US04879296

Reaction notes

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