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

HRID 1086813Notes

Reaction equation

HRID 1086813 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.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

5

Reactant 2

HCID 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 535.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

6-Amino-1-methyl-3-n-propyluracil (13.2 g, 7.3 mmol) was dissolved in 10-15 ml of acetic acid and the solution was warmed on a hot plate to 60-70° C. Then, with stirring, a solution of sodium nitrite (5.3 g, 7.7 mmol) in 100 ml of water was added in 10 ml portions over 10 minutes. A brownish-purple precipitate formed. The reaction mixture was cooled to 10° C. and the precipitate was collected by vacuum filtration, washed with 10 ml of acetone, and air-dried to give 8.3 g (55%) of 6-amino-1-methyl-5-nitroso-3-propyluracil as a purple solid. 1H NMR (DMSO-d6 +D2O) δ 0.90 (t, J=7 Hz, 3 H), 1.62 (sextet, J=7 Hz, 2 H), 3.26 (s, 3 H), 3.87 (t J=7 Hz, 2 H).

Workup

  1. customA brownish-purple precipitate formed
  2. temperatureThe reaction mixture was cooled to 10° C.
  3. filtrationthe precipitate was collected by vacuum filtration
  4. washwashed with 10 ml of acetone
  5. customair-dried

Sources & evidence

ORD record
ord-6165a4f7a006444caf02478da706e066
Source dataset
uspto-grants-1991_07
Patent number
US05032593

Reaction notes

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