Benzamidine, hydrochloride → 2-(2-Propoxyphenyl)-8-phenylpurin-6-one

HRID 1532077Notes

Reaction equation

HRID 1532077 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][CH2:18][CH3:19])[NH:5][C:6](=[O:9])[C:7]=1[NH2:8].Cl.[C:21](N)(=N)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C([O-])(=O)C.[Na+]>C(O)C>[CH2:17]([O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:4]1[N:3]=[C:2]2[C:7](=[N:8][C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:1]2)[C:6](=[O:9])[N:5]=1)[CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 80289Benzamidine, hydrochlorideHCID 517045Sodium AcetateHCID 1357098565,6-Diamino-2-(2-propoxyphenyl)pyrimidin-4(3H)-one

Product 1

HCID 212507492-(2-Propoxyphenyl)-8-phenylpurin-6-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
165 °C

Procedure

A mixture of 4,5-diamino-2-(2-propoxyphenyl)-pyrimidine-6-one (1.3 g), benzamidine hydrochloride (2 g) and anhydrous sodium acetate (0.9 g) was heated in an oil bath (temperature 160-170° C.) for 2 hours. The reaction mixture was digested with hot ethanol to give a solid, 0.76 g, m.p. 267-271° C. This was combined with a further sample, 0.2 g, (similarly prepared) and recrystallised from aqueous acetic acid to give the title compound, 0.74 g, m.p. 259-260° C.

Workup

  1. customto give a solid, 0.76 g, m.p. 267-271° C
  2. custom(similarly prepared) and
  3. customrecrystallised from aqueous acetic acid

Sources & evidence

ORD record
ord-606d07fb233e447fb5bdcbe1184c8fb3
Source dataset
uspto-grants-2001_03
Patent number
US06200980B1

Reaction notes

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