Formamidine acetate → HCID 11096993, compound

HRID 1736396Notes

Reaction equation

HRID 1736396 reaction equation
C(O)(=O)C.[CH:5]([NH2:7])=[NH:6].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16][CH:17]([C:22](OC)=[O:23])[C:18](OC)=[O:19].C[O-].[Na+].[Na]>CO>[OH:23][C:22]1[N:7]=[CH:5][NH:6][C:18](=[O:19])[C:17]=1[S:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:9][CH3:8]

Participants

6

Reactant 4

HCID 160693Formamidine acetateHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 22362038Dimethyl (2-methoxy-phenylsulphanyl)malonate

Product 1

HCID 11096993HCID 11096993, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

0.86 g of formamidine acetate and 2 g of dimethyl (2-methoxy -phenylsulfanyl)-malonate (J. Org. Chem. 55, 33-38 [1990]) were added to a sodium methylate solution from 40 ml of MeOH and 0.54 g of sodium. The reaction mixture was stirred at 80° C. for 4 hours and concentrated. The residue was partitioned between toluene and water and the aqueous phase was adjusted to pH 3. The precipitate was filtered off under suction, washed with ether and dried. There was obtained 0.4 g of 6-hydroxy-5-(2-methoxy-phenylsulfanyl)-3,4-dihydro-pyrimidin-4-one. M.p. 291 ° C.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between toluene and water
  3. filtrationThe precipitate was filtered off under suction
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-861b077199fd469c8b88b09f7a56f516
Source dataset
uspto-grants-1996_07
Patent number
US05541186

Reaction notes

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