Formamidine → 5-(o-chlorobenzyl)-6-hydroxy-4(3H)-pyrimidinone

HRID 326715

Reaction equation

[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][CH:5]([C:11](OCC)=[O:12])[C:6](OCC)=[O:7].[CH:20]([NH2:22])=[NH:21]>>[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[CH2:4][C:5]1[C:11](=[O:12])[NH:22][CH:20]=[N:21][C:6]=1[OH:7]

Participants

Reactant 2

HCID 68047Formamidine

HCID 12661049Diethyl 2-(2-chlorobenzyl)malonate

Product 1

HCID 197353375-(o-chlorobenzyl)-6-hydroxy-4(3H)-pyrimidinone

Procedure

Condensation of diethyl o-chlorobenzylmalonate with formamidine yielded 5-(o-chlorobenzyl)-6-hydroxy-4(3H)-pyrimidinone which, by reaction with phosphorus oxychloride, yielded 4,6-chloro-5-(o-chlorobenzyl)pyrimidine, melting point 110°-112° C.

Sources & evidence

ORD record: ord-938cb0896f2a4a44bf376abc087d4d14
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270313

Linked notes

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