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

HRID 1421229Notes

Reaction equation

HRID 1421229 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-diaminouracil

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 resulting solid was collected by filtration, washed with water (75 ml) and resuspended in water (100 ml). After warming to 50° C., sodium dithionite (10 g) was added in portions maintaining the reaction temperature between 50° C. and 55° C. After stirring at 50° C. for an additional 1 hour, the mixture was cooled to room temperature and filtered. The solid was washed with water (2×25 ml), with acetone (2×25 ml) and then dried under vacuum. Yield=5.6 g.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water (75 ml)
  3. additionsodium dithionite (10 g) was added in portions
  4. temperaturemaintaining the reaction temperature between 50° C. and 55° C
  5. stirringAfter stirring at 50° C. for an additional 1 hour
  6. temperaturethe mixture was cooled to room temperature
  7. filtrationfiltered
  8. washThe solid was washed with water (2×25 ml), with acetone (2×25 ml)
  9. customdried under vacuum

Sources & evidence

ORD record
ord-0489ec66f988423c9a8f483b795c0fbc
Source dataset
uspto-grants-2000_06
Patent number
US06075029

Reaction notes

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