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

HRID 1181223Notes

Reaction equation

HRID 1181223 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-cfbf67b949124a4cb55ad84ddbd3b688
Source dataset
uspto-grants-2007_10
Patent number
US07285549B2

Reaction notes

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