Hydrochloric Acid → 1-Butyl-5-nitroso-6-aminouracil

HRID 720620Notes

Reaction equation

HRID 720620 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH2:10][CH3:11])[C:6](=[O:12])[NH:5][C:4](=[O:13])[CH:3]=1.Cl.[N:15]([O-])=[O:16].[Na+].[OH-].[NH4+]>>[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][CH2:10][CH3:11])[C:6](=[O:12])[NH:5][C:4](=[O:13])[C:3]=1[N:15]=[O:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 24289966-Amino-1-butyl-1,2,3,4-tetrahydropyrimidine-2,4-dioneHCID 23668193Sodium Nitrite

Product 1

HCID 107985701-Butyl-5-nitroso-6-aminouracilYield 83%

Conditions

Temperature
25 °C

Procedure

A suspension of 6-amino-1-butyl-1H-pyrimidine-2,4-dione (3.0 g, 16.4 mmol) in a 1N aqueous hydrochloric acid solution (33 mL) at 25° C. was treated with sodium nitrite (1.47 g, 21.32 mmol) in portions. The pH was adjusted to pH=5 by the addition of ammonium hydroxide (22 mL). The reaction was stirred at 25° C. for 10 min. At this time, the resulting solid was collected by filtration, washed with a pH=5 aqueous buffer, and then dried in vacuo to afford 6-amino-1-butyl-5-nitroso-1H-pyrimidine-2,4-dione (2.89 g, 83%) as a purple solid: LR-MS for C8H12N4O3 (M+H)+ at m/z=213.

Workup

  1. filtrationAt this time, the resulting solid was collected by filtration
  2. washwashed with a pH=5 aqueous buffer
  3. customdried in vacuo

Sources & evidence

ORD record
ord-9b6668ecc675499fa365e9a1a2cd8e56
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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