Methanimidamide, hydrochloride (1:1) → HCID 178418881, compound

HRID 1358323Notes

Reaction equation

HRID 1358323 reaction equation
C[O-].[Na+].C[O:5][C:6](=O)[CH:7]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[C:8](OC)=[O:9].Cl.[CH:23]([NH2:25])=[NH:24]>CO>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][C:7]1[C:8]([OH:9])=[N:24][CH:23]=[N:25][C:6]=1[OH:5]

Participants

5

Reactant 3

HCID 10313058Methanimidamide, hydrochloride (1:1)HCID 10942334Sodium MethoxideHCID 12967085Dimethyl 2-(2-methoxyphenoxy)malonate

Product 1

HCID 178418881HCID 178418881, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 5° C. 12.7 g of sodium methylate was added portionwise to a solution of 18.9 g of dimethyl-2-(o-methoxyphenoxy)malonate in 450 ml of methanol. Upon completion of the addition stirring was continued at room temperature for 30 min followed by the addition of 6 g of formamidine hydrochloride. The mixture was stirred at room temperature for 72 h. Eventually, the solvent was removed under reduced pressure and the remaining residue was suspended in diethyl ether. The solid material was filtered off and dissolved in 100 ml of water. The solution was acidified with conc. hydrochloric acid. A white precipitate formed. The precipitate was collected, washed with water and dried to give 15.1 g of 5-(o-methoxyphenoxy)-4,6-dihydroxy-pyrimidine (or a tautomer) as a white powder.

Workup

  1. customAt 5° C
  2. additionUpon completion of the addition
  3. stirringThe mixture was stirred at room temperature for 72 h
  4. customEventually, the solvent was removed under reduced pressure
  5. filtrationThe solid material was filtered off
  6. dissolutiondissolved in 100 ml of water
  7. customA white precipitate formed
  8. customThe precipitate was collected
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-3a6c0672da1a4454b4fabddb5f559c0d
Source dataset
uspto-grants-2003_07
Patent number
US06596719B1

Reaction notes

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