Acetic Acid → 6-Amino-1,3-dibutyl-5-nitroso-2,4(1H,3H)-pyrimidinedione

HRID 965187Notes

Reaction equation

HRID 965187 reaction equation
[CH2:1]([N:5]1[C:12]([NH2:13])=[CH:11][C:9](=[O:10])[N:8]([CH2:14][CH2:15][CH2:16][CH3:17])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4].C(O)(=O)C.Cl.[N:23]([O-])=[O:24].[Na+]>O>[NH2:13][C:12]1[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6](=[O:7])[N:8]([CH2:14][CH2:15][CH2:16][CH3:17])[C:9](=[O:10])[C:11]=1[N:23]=[O:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 99918436-Amino-1,3-dibutyluracilHCID 23668193Sodium Nitrite

Product 1

HCID 3860046-Amino-1,3-dibutyl-5-nitroso-2,4(1H,3H)-pyrimidinedioneYield 82.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 1,3-di-n-butyl-6-amino-uracil g, 112.8 mmol), glacial acetic acid (10 ml), and 6N HCl (18.8 ml) in water (500 ml) was added dropwise a solution of sodium nitrite (7.78, g, 112.8 mmol) in water (30 ml) on ice bath. The reaction mixture was stirred for 30 min. The violet solid was collected by filtration and washed with water (2×20 ml), dried for 2 days at 60° C. in a vacuum oven to yield 6-amino-1,3-di-n-butyl-5-nitroso-uracil (24.99 g, 82.6%), m.p. 199°-205° C.; 1H NMR (CDCl3) δ0.97-1.01 (m, 6H, 2×CH3), 1.36-1.49 (m, 4H, 2×CH2), 1.62-1.74 (m, 4H, 2×CH2), 3.94 (t, J=7.8 Hz, 2H, N--CH2), 4.08 (t, J=7.5 Hz, 2H, N--CH2), 6.46 (br s, 2H, NH2). Anal. Calc'd for C12H20N4O3 : C, 53.72; H, 7.51; N, 20.88; Found: C, 54.37; H, 7.67; N, 20.65.

Workup

  1. filtrationThe violet solid was collected by filtration
  2. washwashed with water (2×20 ml)
  3. customdried for 2 days at 60° C. in a vacuum oven

Sources & evidence

ORD record
ord-e9bfbb4310e1474ca05f4db260b18057
Source dataset
uspto-grants-1998_06
Patent number
US05773423

Reaction notes

Loading…