Acetamidine monohydrochloride → (2-chloro-5-methoxy-phenoxy)-2-methyl-6-hydroxy-4(3H)-pyrimidinone

HRID 486649Notes

Reaction equation

[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:3]=1[O:4]C(C(OC)=O)C(OC)=O.Cl.[C:21]([NH2:24])(=[NH:23])[CH3:22]>>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:3]=1[O:4][N:23]1[C:3](=[O:4])[CH:14]=[C:15]([OH:18])[N:24]=[C:21]1[CH3:22]

Participants

Reactant 2

HCID 67170Acetamidine monohydrochloride

HCID 21803835Dimethyl (2-chloro-5-methoxy-phenoxy)malonate

Product 1

HCID 135992465(2-chloro-5-methoxy-phenoxy)-2-methyl-6-hydroxy-4(3H)-pyrimidinone

Procedure

In analogy to Example 1, paragraph d), dimethyl (2-chloro-5-methoxy-phenoxy)malonate was condensed with acetamidine hydrochloride to give (2-chloro-5-methoxy-phenoxy)-2-methyl-6-hydroxy-4(3H)-pyrimidinone. Therefrom in analogy to Example 1, paragraph e), there was obtained 4,6-dichloro-5-(2-chloro-5-methoxy-phenoxy)-2-methyl-pyrimidine, m.p. 125°-130° C., and therefrom in analogy to Example 1, paragraph f), there was obtained 4-tert-butyl-N-[6-chloro-5-(2-chloro-5-methoxyphenoxy)-2-methyl-pyrimidin-4-yl]-benzenesulfonamide, m.p. 182° C. (from MeOH).

Sources & evidence

ORD record: ord-522c8a663e3b4cd0818828f9237cab4e
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292740

Reaction notes

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