4-Fluorobenzylamine → N-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidine-2-carboxamide

HRID 2426257Notes

Reaction equation

[OH:1][C:2]1[C:7](=[O:8])[N:6]2[CH2:9][CH2:10][CH2:11][CH2:12][C:5]2=[N:4][C:3]=1[C:13]([O:15]C)=O.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1>CO>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:23][C:13]([C:3]2[N:4]=[C:5]3[CH2:12][CH2:11][CH2:10][CH2:9][N:6]3[C:7](=[O:8])[C:2]=2[OH:1])=[O:15])=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of methyl 3-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-2-carboxylate obtained in Step 3b or Step 5a and 4-fluoro-benzylamine (2 eq.) in methanol was stirred and heated to 65° C. for 22 h. The solvent was removed under reduced pressure and the title product was obtained by preparative RP-HPLC, using water (0.1% TFA) and acetonitrile (0.1% TFA) as eluents (column: C18). The pooled product fractions were lyophilized to afford the title compound as a fluffy white material.

Workup

customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-7e1183715f4945f581d10b78d45b6097
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968553B2

Reaction notes

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