Hydrazine hydrate (1:1) → Uracil, 1,3-dimethyl-6-hydrazino-

HRID 1467826Notes

Reaction equation

HRID 1467826 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[CH:3]=1.O.[NH2:13][NH2:14]>C(O)(C)C>[NH:13]([C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[CH:3]=1)[NH2:14]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 814426-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 97642Uracil, 1,3-dimethyl-6-hydrazino-

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of Step 1 intermediate (17 g, 97.34 mmol) and hydrazine hydrate (119 ml) in isopropyl alcohol (280 ml) were refluxed for 1 h. The excess of solvent was removed under reduced pressure, solid obtained was filtered, washed with methanol (25 ml) and dried to obtain 8.1 g of the product as white solid; 1H NMR (300 MHz, DMSO-d6): δ 3.09 (s, 3H), 3.21 (s, 3H), 4.37 (br s, 2H), 5.10 (s, 1H), 8.02 (br s, 1H).

Workup

  1. customThe excess of solvent was removed under reduced pressure, solid
  2. customobtained
  3. filtrationwas filtered
  4. washwashed with methanol (25 ml)
  5. customdried

Sources & evidence

ORD record
ord-5b4c8316b6634c9bbc223e20773927fd
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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