Acetamidine monohydrochloride → HCID 178418769, compound

HRID 10240

Reaction equation

HRID 10240 reaction equation
CO[C:3](=[O:18])[CH:4]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17])[C:5]([O:7]C)=O.C[O-].[Na+].Cl.[C:23]([NH2:26])(=[NH:25])[CH3:24]>CO>[CH3:17][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[O:9][C:4]1[C:3]([OH:18])=[N:25][C:23]([CH3:24])=[N:26][C:5]=1[OH:7]

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium MethoxideHCID 12967085Dimethyl 2-(2-methoxyphenoxy)malonate

Product 1

HCID 178418769HCID 178418769, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of dimethyl-(o-methoxyphenoxy)malonate (10 g) in dry methanol (80 ml) was cooled to 0° C. Sodium methylate (6.71 g) was added portionwise. To the suspension was added of acetamidine hydrochloride (2.84 g) and the mixture was stirred overnight at r.t. The solvent was removed under reduced pressure and the residue was suspended in diethyl ether (100 ml). The solid was filtered off, washed with another portion of diethyl ether (100 ml) and dissolved in water (50 ml). The pH was adjusted to 4 by adding glacial acetic acid (25 ml). The white precipitate that formed was filtered off, washed with water and dried to yield 5-(o-methoxyphenoxy)-4,6-dihydroxy-2-methyl-pyrimidine (5.17 g) (or a tautomer) as a white powder.

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationThe solid was filtered off
  3. washwashed with another portion of diethyl ether (100 ml)
  4. dissolutiondissolved in water (50 ml)
  5. additionby adding glacial acetic acid (25 ml)
  6. customThe white precipitate that formed
  7. filtrationwas filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-ba7cc86b1c11497fa2e3875ac0edb856
Source dataset
uspto-grants-2006_08
Patent number
US07094781B2

Linked notes

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