6-Amino-3-methyl-5-nitroso-1-phenylpyrimidine-2,4(1H,3H)-dione → 5,6-Diamino-3-methyl-1-phenyluracil

HRID 2258472Notes

Reaction equation

[NH2:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6](=[O:14])[N:5]([CH3:15])[C:4](=[O:16])[C:3]=1[N:17]=O>[Pd].CO>[NH2:17][C:3]1[C:4](=[O:16])[N:5]([CH3:15])[C:6](=[O:14])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]=1[NH2:1]

Participants

Conditions

Temperature: 70 °C

Procedure

The obtained 6-amino-3-methyl-5-nitroso-1-phenyluracil (0.25 g) and 5% Pd/C (20 mg) were added to 50 ml of methanol and purging with hydrogen gas was performed, followed by stirring at 70° C. for 2.5 hours. The reaction mixture was filtered while hot to give a filtrate. The solvent methanol was distilled off from the filtrate to yield 5,6-diamino-3-methyl-1-phenyluracil (yield: 0.2 g, or 86% based on 6-amino-3-methyl-5-nitroso-1-phenyluracil).

Workup

custompurging with hydrogen gas
filtrationThe reaction mixture was filtered while hot
customto give a filtrate
distillationThe solvent methanol was distilled off from the filtrate

Sources & evidence

ORD record: ord-cff54a268bd942c5ad1d0d7274a2446c
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05661153

Reaction notes

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