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

HRID 10241

Reaction equation

HRID 10241 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. sodium methylate (12.7 g) was added portionwise to a solution of dimethyl-(o-methoxyphenoxy)malonate (18.9 g) in methanol (450 ml). Upon completion of the addition stirring was continued at r.t. for 30 min followed by the addition of formamidine hydrochloride (6 g). The mixture was stirred at r.t. 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 water (100 ml). The solution was acidified with conc. hydrochloric acid. A white precipitate formed. The precipitate was collected, washed with water and dried to give 5-(o-methoxyphenoxy)-4,6-dihydroxy-pyrimidine (15.1 g) (or a tautomer) as a white powder.

Workup

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

Sources & evidence

ORD record
ord-81e84f2f46764e7283256657b7d79e0f
Source dataset
uspto-grants-2006_08
Patent number
US07094781B2

Linked notes

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