Hydrochloric Acid → 6-Amino-1-isobutyl-3-methyl-5-nitroso-2-thioxo-1H-pyrimidin-4-one

HRID 31066Notes

Reaction equation

HRID 31066 reaction equation
[N:1]([O-:3])=O.[Na+].[NH2:5][C:6]1[N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:10](=[S:16])[N:9]([CH3:17])[C:8](=[O:18])[CH:7]=1.Cl>O.C(O)C>[NH2:5][C:6]1[N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:10](=[S:16])[N:9]([CH3:17])[C:8](=[O:18])[C:7]=1[N:1]=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 866010566-amino-1-isobutyl-3-methyl-2-thioxo-1H-pyrimidin-4-one

Product 1

HCID 866010576-Amino-1-isobutyl-3-methyl-5-nitroso-2-thioxo-1H-pyrimidin-4-oneYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Sodium nitrite (0.34 g, 4.9 mmol) in water (1.5 mL) was added to a solution of the amine (1.00 g, 4.7 mmol) in ethanol (7.0 mL) at room temperature. 5M Hydrochloric acid (1.0 mL, 4.9 mmol) was added and the resulting dark red reaction mixture was stirred at room temperature for 2 h. Ethanol (20 mL) was added and the red crystals were filtered off and washed with diethyl ether. Drying of the crystals gave the title compound (0.68 g, 60%).

Workup

  1. customthe resulting dark red reaction mixture
  2. filtrationthe red crystals were filtered off
  3. washwashed with diethyl ether
  4. customDrying of the crystals

Sources & evidence

ORD record
ord-1fe0a1b1f3914f6c9eadf529b5b21b14
Source dataset
uspto-grants-2008_09
Patent number
US07425560B2

Reaction notes

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