Ammonia → 5-Aminouracil

HRID 1043555Notes

Reaction equation

HRID 1043555 reaction equation
N.[N+:2]([C:5]1[C:6](=[O:12])[NH:7][C:8](=[O:11])[NH:9][CH:10]=1)([O-])=O>O>[NH2:2][C:5]1[C:6](=[O:12])[NH:7][C:8](=[O:11])[NH:9][CH:10]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 691355-Nitrouracil

Product 1

HCID 136115-Aminouracil

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Into a 5-L 4-necked round-bottom flask were placed water (2.871 L), ammonia (116.1 mL) and 5-nitropyrimidine-2,4(1H,3H)-dione (180 g, 1.15 mol, 1.00 equiv). This was followed by the addition of Na2S2O2 (860 g, 6.06 mol, 4.30 equiv) in several batches. The pH value of the solution was adjusted to 8 with ammonia (25%). The resulting solution was stirred for 3 h (hours) at 75° C. The reaction mixture was cooled to 15° C. with an ice/water bath. The solid was collected by filtration. This resulted in 118 g (81%) of 5-aminopyrimidine-2,4(1H,3H)-dione 1 as a yellow solid (see Scheme 1).

Workup

  1. customInto a 5-L 4-necked round-bottom flask were placed
  2. temperatureThe reaction mixture was cooled to 15° C. with an ice/water bath
  3. filtrationThe solid was collected by filtration
  4. customThis resulted in 118 g (81%) of 5-aminopyrimidine-2,4(1H,3H)-dione 1 as a yellow solid (see Scheme 1)

Sources & evidence

ORD record
ord-806d22519b394529a2a8b4188d7e8cb7
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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