Nitric Acid → HCID 178433493, compound

HRID 229327Notes

Reaction equation

HRID 229327 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[N+:10]([O-])([OH:12])=[O:11]>FC(F)(F)C(O)=O>[CH3:9][C:4]1[N:5]=[C:6]([OH:8])[C:7]([N+:10]([O-:12])=[O:11])=[C:2]([OH:1])[N:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178418389HCID 178418389, compound

Product 1

HCID 178433493HCID 178433493, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Powdered 4,6-dihydroxy-2-methylpyrimidine (9 g, 71 mmol) was dissolved in trifluoroacetic acid (54 mL). The reaction mixture was cooled in ice-water as nitric acid (4.3 mL) was added dropwise over a period of 30 minutes. During addition the internal temperature was maintained below 15° C. After the addition, the cooling was removed and the reaction stirred overnight. Water (50 mL) was added to the reaction mixture and the resulting solid was filtered and dried under vacuum to obtain 2-methyl-5-nitropyrimidine-4,6-diol (5.8 g). 1H NMR (400 MHz, DMSO-d6): δ 12.97 (br, 2H), 2.32 (s, 3H). MS (m/z) 172 (M+1).

Workup

  1. additionwas added dropwise over a period of 30 minutes
  2. additionDuring addition the internal temperature
  3. temperaturewas maintained below 15° C
  4. additionAfter the addition
  5. customthe cooling was removed
  6. additionWater (50 mL) was added to the reaction mixture
  7. filtrationthe resulting solid was filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-235eb10a10b546d48ae1feaba61f9a63
Source dataset
uspto-grants-2009_07
Patent number
US07563787B2

Reaction notes

Loading…