Nitric Acid → HCID 178526744, compound

HRID 876951Notes

Reaction equation

HRID 876951 reaction equation
N[C:2]1[N:7]=[C:6](O)[CH:5]=[C:4](Cl)[N:3]=1.[N+:10]([O-])([OH:12])=[O:11].S(=O)(=O)(O)[OH:15]>>[N+:10]([C:4]1[CH:5]=[CH:6][N:7]=[C:2]([OH:15])[N:3]=1)([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 944Nitric Acid3×HCID 1118Sulfuric AcidHCID 1785089742-amino-6-chloro-1H-pyrimidin-4-one

Product 1

HCID 178526744HCID 178526744, compoundYield 98%

Conditions

Temperature
20 °C

Procedure

250 mL (5 volumes) of concentrated sulfuric acid was stirred in a 1000 mL round bottom flask (22° C.). To this, 2-amino-6-chloro-4-pyrimidinol (50 g) was added in portions. The temperature increased rapidly with early additions, stabilizing at a temperature of 40° C. Later additions had less effect on the temperature, a maximum of approx. 45° C. being recorded. Prior to addition of fuming nitric acid (45 mL, 0.9 volumes), the mixture was cooled (using an ice bath) to 20° C. In portions of roughly 1.5 mL (reflecting pipette volume), nitric acid was added dropwise at a steady rate (ca. 1 min between each portion). Early portions had the greatest effect on the temperature, the controlled exotherms reaching a temperature of approx. 26° C. before returning to 20° C. under the influence of the ice bath. Later portions had little effect, and the temperature was maintained at approx. 21° C. After 45 mL of fuming nitric acid had been added in this way, the mixture was allowed to stir for 2 hr (during this period the ice bath was removed and the temperature stabilised at room temperature ca. 22° C.). The entire mixture was poured onto stirred ice/water (1200 mL) and the resulting yellow solid filtered under vacuum. The product was washed in succession with water (600 mL), ethanol (600 mL) and diethylether (600 mL). This method gave 63.5 g (98% yield) of the required nitro-pyrimidinol.

Workup

  1. temperatureThe temperature increased rapidly with early additions
  2. customstabilizing at a temperature of 40° C
  3. customa maximum of approx. 45° C.
  4. customa temperature of approx. 26° C.
  5. temperaturethe temperature was maintained at approx. 21° C
  6. customwas removed
  7. customstabilised at room temperature ca. 22° C.
  8. additionThe entire mixture was poured
  9. filtrationthe resulting yellow solid filtered under vacuum
  10. washThe product was washed in succession with water (600 mL), ethanol (600 mL) and diethylether (600 mL)

Sources & evidence

ORD record
ord-27e2b67c9bc3490f9cbb52fe8b4ab4fe
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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