Acetic Acid → 3-Methyl-4,5-diaminouracil

HRID 1835701Notes

Reaction equation

HRID 1835701 reaction equation
C(O)(=O)C.[NH2:5][C:6]1[N:11]([CH3:12])[C:10](=[O:13])[NH:9][C:8](=[O:14])[CH:7]=1.[N:15]([O-])=O.[Na+]>O>[NH2:15][C:7]1[C:8](=[O:14])[NH:9][C:10](=[O:13])[N:11]([CH3:12])[C:6]=1[NH2:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 755206-Amino-1-methyluracilHCID 23668193Sodium Nitrite

Product 1

HCID 1571843-Methyl-4,5-diaminouracilYield 71.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Glacial acetic acid (4.5 ml, 75 mmol) was added to a suspension of 6-amino-1-methyluracil (5.66 g, 50 mmol) in hot water (100 ml). Sodium nitrite (4.14 g) was added in portions and the reaction mixture was stirred for 1 hour. The precipitate was collected by filtration, washed with water (75 ml) and then suspended in water (100 ml). The mixture was warmed to 50° C. and sodium dithionite (10 g) was added in portions keeping the temperature of the reaction between 50-55° C. The mixture was stirred at 50° C. for 1 hr and then cooled to room temperature and filtered. The solid was washed with water (2×25 ml), acetone (2×25 ml) and dried under vacuum to provide 5,6-diamino-1-methyluracil (5.6 g).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water (75 ml)
  3. additionsodium dithionite (10 g) was added in portions
  4. customthe temperature of the reaction between 50-55° C
  5. stirringThe mixture was stirred at 50° C. for 1 hr
  6. temperaturecooled to room temperature
  7. filtrationfiltered
  8. washThe solid was washed with water (2×25 ml), acetone (2×25 ml)
  9. customdried under vacuum

Sources & evidence

ORD record
ord-5c7e01d4d3064095b15473f43ea20fdb
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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