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

HRID 883554
Notes
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Reaction equation

HRID 883554 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 962
Water
Solvent

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-4a1b35fa83574166b1335dbbed4eaf79
Source dataset
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08236951B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes