Guanidine Hydrochloride → HCID 178508987, compound

HRID 1492143Notes

Reaction equation

[F:1][CH:2]([C:7]([O:9]C)=O)[C:3](OC)=[O:4].Cl.[NH2:12][C:13]([NH2:15])=[NH:14]>>[OH:9][C:7]1[C:2]([F:1])=[C:3]([OH:4])[N:14]=[C:13]([NH2:15])[N:12]=1

Participants

Reactant 2

HCID 5742Guanidine Hydrochloride

HCID 2737111Dimethyl fluoromalonate

Product 1

HCID 178508987HCID 178508987, compound

Procedure

Commercially available dimethyl fluoromalonate (1) (or the diethyl ester) is condensed with guanidine hydrochloride (2) to yield 4,6-dihydroxy-5-fluoro-2-pyrimidineamine (3). This product (3) was converted to the dichloride (4) with POCl3 /2-picoline. Introduction of the 4-amino group was carried out undersealed tube conditions to give (5). Oxidation of (5) with MCPBA formed the N-oxide (6) which was smoothly converted to the 5-fluoro minoxidil with piperidine in refluxing ethanol.

Sources & evidence

ORD record: ord-1b804149613648a190833849ba619b6e
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05373012

Reaction notes

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