Sulfuric Acid → HCID 86631108, compound

HRID 912647Notes

Reaction equation

HRID 912647 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:6](=[S:15])[NH:5][C:4](=[O:16])[CH:3]=1.[N:17]([O-])=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+].S(=O)(=O)(O)O>C(O)(=O)C>[NH2:17][C:3]1[C:4](=[O:16])[NH:5][C:6](=[S:15])[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 24489Sodium DithioniteHCID 4870887HCID 4870887, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 86631108HCID 86631108, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

6-Amino-1-(pyridin-2-ylmethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (0.60 g, 2.56 mmol, obtained from Example 1(b)) was dissolved in acetic acid (90% aq., 10 mL) and was heated at 75° C. for 5 minutes. Sodium nitrite (0.20 g, 2.95 mmol) was added and heating was continued for another 30 minutes. The solvent was removed in vacuo and the residue was suspended in water (6 mL), and ammonia (32% aq., 6 mL) was added. The reaction mixture was heated at 75° C. and sodium dithionite (1.1 g, 6.4 mmol) was added and the resulting mixture was continued stirring at 75° C. for 5 minutes, and then stirred at r.t. for 30 minutes. After adjusting the solution to neutral pH with 2M sulfuric acid the precipitated solid was collected by filtration, washed with a small amount of water and dried, giving the title compound (0.331 g, 52%) as a solid. The crude product was used in the next step without further purification.

Workup

  1. temperatureheating
  2. customThe solvent was removed in vacuo
  3. additionammonia (32% aq., 6 mL) was added
  4. temperatureThe reaction mixture was heated at 75° C.
  5. stirringstirred at r.t. for 30 minutes
  6. filtrationwas collected by filtration
  7. washwashed with a small amount of water
  8. customdried

Sources & evidence

ORD record
ord-b6c02fcd92d54a3b825dc4ff558079b6
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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