Acetic Acid → HCID 178460811, compound

HRID 537017Notes

Reaction equation

HRID 537017 reaction equation
C(O)(=O)C.[N+:5]([O-:8])(O)=[O:6].[CH2:9]([S:12][C:13]1[N:18]=[C:17]([OH:19])[CH:16]=[C:15]([OH:20])[N:14]=1)[CH2:10][CH3:11]>O>[N+:5]([C:16]1[C:15]([OH:20])=[N:14][C:13]([S:12][CH2:9][CH2:10][CH3:11])=[N:18][C:17]=1[OH:19])([O-:8])=[O:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 1784608102-(Propylthio)pyrimidine-4,6-diol

Product 1

HCID 178460811HCID 178460811, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic acid (125 ml) and fuming nitric acid (42.5 ml) were placed in a clean and dry reaction assembly, followed by the addition of 2-propylthio-pyrimidine-4,6-diol (50 g) over a period of 60 minutes at 30-35° C. and with stirring for 1 hour. After completion of the reaction, monitored by TLC, the reaction mass was slowly added to water (250 ml) with maintaining the temperature at below 25° C. The resulting slurry was stirred for 1 hour at 20-25° C. The product was isolated by filtration and washed successively with water (3×100 ml). The wet product was dried under reduced pressure at 40-45° C. to produce 48.28 g of 5-nitro-2-propylthiopyrimidine-4,6-diol as a off-white powder (Purity by HPLC: 99.02 area-%).

Workup

  1. customdry
  2. customreaction assembly
  3. customAfter completion of the reaction
  4. temperaturewith maintaining the temperature at below 25° C
  5. stirringThe resulting slurry was stirred for 1 hour at 20-25° C
  6. customThe product was isolated by filtration
  7. washwashed successively with water (3×100 ml)
  8. customThe wet product was dried under reduced pressure at 40-45° C.

Sources & evidence

ORD record
ord-4036542ab94d45fa9575ea16eb8a1f20
Source dataset
uspto-grants-2014_10
Patent number
US08859769B2

Reaction notes

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