Formamidine acetate → HCID 178491343, compound

HRID 326699Notes

Reaction equation

HRID 326699 reaction equation
C(O)(=O)C.[CH:5]([NH2:7])=[NH:6].[Na].[CH3:9][O:10][C:11]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[C:12]=1[CH2:13][CH:14]([C:20](OCC)=[O:21])[C:15](OCC)=[O:16]>C(O)C>[CH3:30][O:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:11]([O:10][CH3:9])[C:12]=1[CH2:13][C:14]1[C:15]([OH:16])=[N:6][CH:5]=[N:7][C:20]=1[OH:21]

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 5360545SodiumHCID 54492584Diethyl (2,6-dimethoxybenzyl)malonate

Product 1

HCID 178491343HCID 178491343, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
25 °C

Procedure

0.23 g of formamidine acetate in 15 ml of ethanol was added to 0.14 g of sodium in 15 ml of ethanol. The reaction mixture was stirred 25° C. for 30 minutes and treated dropwise with 0.62 g of diethyl (2,6-dimethoxybenzyl)malonate in 10 ml of ethanol. Starting material was no longer present after 2 days. The residue was removed by filtration under suction, dissolved in a small amount of water and acidified with 1N HCl. The precipitated crystals were removed by filtration under suction and dried at 90° C. in a high vacuum. There was obtained 0.175 g of 5-(2,6-dimethoxy-benzyl)-4,6-pyrimidinediol of melting point >245° C.

Workup

  1. customafter 2 days
  2. customThe residue was removed by filtration under suction
  3. dissolutiondissolved in a small amount of water
  4. customThe precipitated crystals were removed by filtration under suction
  5. customdried at 90° C. in a high vacuum

Sources & evidence

ORD record
ord-1da4ff1baa5c497cb6eedde7b6e1807b
Source dataset
uspto-grants-1993_12
Patent number
US05270313

Reaction notes

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