Uracil, 6-amino-3-methyl-1-propyl- → HCID 14425321, compound

HRID 1086814Notes

Reaction equation

HRID 1086814 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH3:12])[C:4](=[O:13])[CH:3]=1.[N:14]([O-])=[O:15].[Na+]>C(O)(=O)C.O>[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH3:12])[C:4](=[O:13])[C:3]=1[N:14]=[O:15]

Participants

5

Reactant 2

HCID 104563Uracil, 6-amino-3-methyl-1-propyl-HCID 23668193Sodium Nitrite

Product 1

HCID 14425321HCID 14425321, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

6-Amino-3-methyl-1-n-propyluracil (10.46 g, 57.8 mmol) was dissolved in 10 ml of acetic acid at 90° C. Then, with stirring, a solution of sodium nitrite (4.19 g, 60.8 mmol) in 100 ml of water was added in 10 ml portions over 5 minutes. A purple color formed immediately followed by a purple precipitate. The mixture was cooled in the freezer for 20 minutes and then the precipitate was collected by vacuum filtration, washed with water (2×30 ml) and acetone (2×10 ml), and air-dried to give 6-amino-3-methyl-5-nitroso-1-n-propyluracil as purple needles (10.02 g, 83%). 1H NMR (DMSO-d6 +D2O) δ0.89 (t, J=8 Hz, 3 H), 1.55 (sextet, J=8 Hz, 2 H), 3.27 (s, 3 H), 3.80 (t, J=8 Hz, 2 H).

Workup

  1. customA purple color formed immediately
  2. temperatureThe mixture was cooled in the freezer for 20 minutes
  3. filtrationthe precipitate was collected by vacuum filtration
  4. washwashed with water (2×30 ml) and acetone (2×10 ml)
  5. customair-dried

Sources & evidence

ORD record
ord-4ae0e829900845139036fc8ae49340f3
Source dataset
uspto-grants-1991_07
Patent number
US05032593

Reaction notes

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