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Pyridine-4-amidine hydrochloride → 5-(2-Methoxyphenoxy)-2-(4-pyridyl)-tetrahydropyrimidine-4,6-dion

HRID 8601
Notes
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Reaction equation

HRID 8601 reaction equation
C[O-].[Na+].C[O:5][C:6](=[O:21])[CH:7]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])[C:8]([O:10]C)=[O:9].Cl.[C:23]([C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)(=[NH:25])[NH2:24]>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:6]([OH:21])=[N:24][C:23]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[N:25][C:8]=1[OH:10].[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][CH:7]1[C:6](=[O:5])[NH:24][CH:23]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[NH:25][C:8]1=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 2776844Pyridine-4-amidine hydrochlorideHCID 10942334Sodium MethoxideHCID 12967085Dimethyl 2-(2-methoxyphenoxy)malonate

Product 2

HCID 219795945-(2-Methoxyphenoxy)-2-(4-pyridyl)-tetrahydropyrimidine-4,6-dionHCID 178419092HCID 178419092, compound

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent
2×

Procedure

To a stirred solution of sodium methylate (9.7 g) in methanol (100 ml) a solution of dimethyl-(2-methoxyphenoxy)malonate (21.7 g) in methanol (50 ml) was added within 15 min and stirring was continued for 30 min followed by the addition of 4-amidino-pyridine hydrochloride (15 g, Referential Example 2) followed by stirring at room temperature for 20 h. The reaction mixture was concentrated in vacuo. The solid residue was stirred with diethyl ether. The obtained powder was filtered off and dissolved in water (300 ml). Acetic acid was added to pH=4. The precipitated product was filtered off, washed with water and dried in vacuo at 500C. 5-(o-methoxyphenoxy)4,6-dihydroxy-2-(4-pyridyl)pyrimidine (20.1 g, possibly also present as the tautomeric 5-(2-methoxyphenoxy)-2-(4-pyridyl)-tetrahydropyrimidine-4,6-dion) was obtained as a white powder.

Workup

  1. stirringby stirring at room temperature for 20 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. stirringThe solid residue was stirred with diethyl ether
  4. filtrationThe obtained powder was filtered off
  5. dissolutiondissolved in water (300 ml)
  6. additionAcetic acid was added to pH=4
  7. filtrationThe precipitated product was filtered off
  8. washwashed with water
  9. dry with materialdried in vacuo at 500C

Sources & evidence

ORD record
ord-505c53311be54335b86ddee8a50835c0
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091201B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes