Nitric Acid → HCID 178433493, compound

HRID 1640425Notes

Reaction equation

HRID 1640425 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-afe1b01225054c44a0563ab46160da68
Source dataset
uspto-grants-2012_02
Patent number
US08114870B2

Reaction notes

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