Hydrochloric Acid → 6-amino-3-(2-fluoro-benzyl)-5-nitroso-1H-pyrimidine-2,4-dione

HRID 858036Notes

Reaction equation

HRID 858036 reaction equation
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[C:4](=[O:17])[CH:3]=1.Cl.[N:19]([O-])=[O:20].[Na+].[OH-].[NH4+]>O>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[C:4](=[O:17])[C:3]=1[N:19]=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 23668193Sodium NitriteHCID 454973636-amino-3-(2-fluorobenzyl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 587628356-amino-3-(2-fluoro-benzyl)-5-nitroso-1H-pyrimidine-2,4-dioneYield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 6-amino-3-(2-fluoro-benzyl)-1H-pyrimidine-2,4-dione (2.4 g, 10.6 mmol) in a 1.0N aqueous hydrochloric acid solution at 25° C. was treated with a solution of sodium nitrite (0.95 g, 13.78 mmol) in water (10 mL). The mixture was stirred at 25° C. for 3 h. At this time, the reaction was brought to pH=5 through treatment with a 1.0N aqueous ammonium hydroxide solution. The resulting solid was collected by filtration and washed with cold water to afford 6-amino-3-(2-fluoro-benzyl)-5-nitroso-1H-pyrimidine-2,4-dione (2.58 g, 92%); LRMS for C11H9FN4O3 (M+H)+ at m/z=265.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with cold water

Sources & evidence

ORD record
ord-0e1850f463e747ef9295ac804a1a495a
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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