Acetamidine monohydrochloride → HCID 178418769, compound

HRID 2085081Notes

Reaction equation

HRID 2085081 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 10 g of dimethyl-(o-methoxyphenoxy)malonate (Example 1b) in 80 ml dry methanol was cooled to 0° C. 6.71 g of sodium methylate was added portionenwise. To the suspension was added 2.84 g of acetamidine hydrochloride and the mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure and the residue was suspended in 100 ml of diethyl ether. The solid was filtered off, washed with another portion of 100 ml of diethyl ether and dissolved in 50 ml of water. The pH was adjusted to 4 by adding 25 ml of glacial acetic acid. The white precipitate that formed was filtered off, washed with water and dried to yield 5.17 g of 5-(o-methoxyphenoxy)-4,6-dihydroxy-2-methyl-pyrimidine (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 100 ml of diethyl ether
  4. dissolutiondissolved in 50 ml of water
  5. additionby adding 25 ml of glacial acetic acid
  6. customThe white precipitate that formed
  7. filtrationwas filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-eab1ffd049c04bde8e2f3cc6f0bead7e
Source dataset
uspto-grants-2004_04
Patent number
US06720322B2

Reaction notes

Loading…