Sodium Bisulfate → 5,6-Diamino-1-butylpyrimidine-2,4(1H,3H)-dione

HRID 720621Notes

Reaction equation

HRID 720621 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])[C:3]=1[N:14]=O.OS([O-])(=O)=O.[Na+]>O>[NH2:14][C:3]1[C:4](=[O:13])[NH:5][C:6](=[O:12])[N:7]([CH2:8][CH2:9][CH2:10][CH3:11])[C:2]=1[NH2:1]

Participants

4

Reactant 2

HCID 516919Sodium BisulfateHCID 107985701-Butyl-5-nitroso-6-aminouracil

Product 1

HCID 105841085,6-Diamino-1-butylpyrimidine-2,4(1H,3H)-dioneYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A suspension of 6-amino-1-butyl-5-nitroso-1H-pyrimidine-2,4-dione (500 mg, 2.36 mmol) in water (8.3 mL) at 85° C. was treated with sodium hydrosulfate (1.23 g, 7.08 mmol). The reaction was stirred at 85° C. for 20 min. At this time, the reaction was cooled to 0° C. The resulting green solid was collected by filtration, washed with water, and air dried for 30 min to afford 5,6-diamino-1-butyl-1H-pyrimidine-2,4-dione (304 mg, 65%) as a pale green solid: LR-MS for C8H14N4O2 (M+H)+ at m/z=199.

Workup

  1. temperatureAt this time, the reaction was cooled to 0° C
  2. filtrationThe resulting green solid was collected by filtration
  3. washwashed with water, and air
  4. customdried for 30 min

Sources & evidence

ORD record
ord-c0f6da689c39466a8feff06839385f06
Source dataset
uspto-grants-2006_11
Patent number
US07135475B2

Reaction notes

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