Acetic Acid → HCID 10537219, compound

HRID 600563Notes

Reaction equation

HRID 600563 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:6](=[O:13])[NH:5][C:4](=[O:14])[CH:3]=1.C(O)(=O)C.[N:19]([O-])=[O:20].[Na+]>O>[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[C:6](=[O:13])[NH:5][C:4](=[O:14])[C:3]=1[N:19]=[O:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10845599HCID 10845599, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 10537219HCID 10537219, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirring mixture of 6-amino-1-pentylpyrimidine-2,4(1H,3H)-dione (4.0 g, 0.020 mol) and acetic acid (20 mL, 0.4 mol) in water (20 mL) was slowly added sodium nitrite (1.5 g, 0.022 mol). Stirring was continued at room temperature for 2 h at which time the reaction mixture became pink and precipitate formed. The reaction mixture was concentrated under reduced pressure. The resulting residue was dissolved in aqueous NaOH solution and extracted with methylene chloride to remove byproducts. The aqueous solution was neutralized with HCl and concentrated. The residue was treated with methanol and filtered. The filtrate was concentrated to give the desired product as pink solid. LCMS calculated for C9H15N4O3 (M+H): 227.1. found: 227.1 (M+H), 249.1 (M+Na).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in aqueous NaOH solution
  3. extractionextracted with methylene chloride
  4. customto remove byproducts
  5. concentrationconcentrated
  6. additionThe residue was treated with methanol
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9aa51c31efbc4b6d87b3626e31456429
Source dataset
uspto-grants-2011_03
Patent number
US07902205B2

Reaction notes

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