Water → HCID 86601060, compound

HRID 883557Notes

Reaction equation

HRID 883557 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][O:10][CH3:11])[C:6](=[S:12])[NH:5][C:4](=[O:13])[CH:3]=1.[N:14]([O-])=[O:15].[Na+].O>C(O)(=O)C>[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][O:10][CH3:11])[C:6](=[S:12])[NH:5][C:4](=[O:13])[C:3]=1[N:14]=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 31844116-amino-1-(2-methoxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-oneHCID 23668193Sodium Nitrite

Product 1

HCID 86601060HCID 86601060, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
75 °C

Procedure

6-Amino-1-(2-methoxy-ethyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one (1.0 g, 5.0 mmol) was suspended in 10% acetic acid (20 mL). Sodium nitrite (0.38 g, 5.5 mmol) was added and the resulting mixture was heated at 75° C. for 1 h. The reaction mixture became first pink and then purple. Water (20 mL) was added and the reaction mixture was put in the fridge overnight. The purple solid was collected by filtration and washed with water to give the title compound (0.42 g, 37%). A second crop of product (0.22 g, 19%) was obtained by reducing the volume of the purple filtrate. The crude product was used in the following step without further purification.

Workup

  1. customwas put in the fridge overnight
  2. filtrationThe purple solid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-b765499c01494cae8e0bb704104a9bf3
Source dataset
uspto-grants-2012_08
Patent number
US08236951B2

Reaction notes

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