4-Methoxybenzamidine Hydrochloride → 2-(p-methoxyphenyl)-5-(o-methoxyphenoxy)-6-hydroxy-4(3H)-pyrimidinone

HRID 486647

Reaction equation

HRID 486647 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][CH:16]=[CH:15][C:4]=1[O:5][CH:6]([C:11]([O:13]C)=O)[C:7]([O:9]C)=O.Cl.[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH2:28])=[NH:27])=[CH:24][CH:23]=1>>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:26]2[NH:28][C:7](=[O:9])[C:6]([O:5][C:4]3[CH:15]=[CH:16][CH:17]=[CH:18][C:3]=3[O:2][CH3:1])=[C:11]([OH:13])[N:27]=2)=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 123262194-Methoxybenzamidine HydrochlorideHCID 12967085Dimethyl 2-(2-methoxyphenoxy)malonate

Product 1

HCID 190958292-(p-methoxyphenyl)-5-(o-methoxyphenoxy)-6-hydroxy-4(3H)-pyrimidinone

Procedure

In analogy to Example 1, paragraph d), 7.63 g of dimethyl (o-methoxyphenoxy)malonate and 5.6 g of p-methoxy-benzamidine hydrochloride were condensed to give 2-(p-methoxyphenyl)-5-(o-methoxyphenoxy)-6-hydroxy-4(3H)-pyrimidinone. Reaction of this compound in analogy to Example 1, paragraph e), yielded 4,6-dichloro-2-(p-methoxyphenyl)-5-(o-methoxyphenoxy)-pyrimidine, m.p. 113°-114° C., from which in analogy to Example 1, paragraph f), there was obtained p-tert-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-2-(p-methoxyphenyl)-4-pyrimidinyl]benzenesulfonamide, m.p. 221°-222° C.

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-2e62db721a40488b92e53bb17a66972f
Source dataset
uspto-grants-1994_03
Patent number
US05292740

Linked notes

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