5-Chloro-2-hydroxy-3-methoxybenzaldehyde → 6-[4-(5-Chloro-2-hydroxy-3-methoxy-benzyl)-piperazin-1-yl]-3H-pyrimidin-4-one

HRID 1993456Notes

Reaction equation

HRID 1993456 reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[CH:16]=[C:17]([O:24][CH3:25])[C:18]([OH:23])=[C:19]([CH:22]=1)[CH:20]=O>>[Cl:14][C:15]1[CH:16]=[C:17]([O:24][CH3:25])[C:18]([OH:23])=[C:19]([CH:22]=1)[CH2:20][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[N:12]=[CH:11][NH:10][C:9](=[O:13])[CH:8]=2)[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 51510865-Chloro-2-hydroxy-3-methoxybenzaldehydeHCID 1361025406-piperazin-1-yl-3H-pyrimidin-4-one2×

Product 1

HCID 1361025696-[4-(5-Chloro-2-hydroxy-3-methoxy-benzyl)-piperazin-1-yl]-3H-pyrimidin-4-one

Procedure

6-[4-(5-Chloro-2-hydroxy-3-methoxy-benzyl)-piperazin-1-yl]-3H-pyrimidin-4-one was prepared using Procedure B from 6-piperazin-1-yl-3H-pyrimidin-4-one (Intermediate 4) and 5-chloro-2-hydroxy-3-methoxybenzaldehyde (available from Aldrich). 1H NMR (400 MHz, CDCl3) δ 2.50-2.55 (m, 4H), 3.60-3.66 (m, 4H), 3.70 (s, 2H), 3.88 (s, 3H), 5.39 (s, 1H), 6.61-6.62 (m, 1H), 6.80-6.81 (m, 1H), 7.84 (s, 1H), 12.40 (br s, 1H). Mass spectrum (ES) MH+=351.

Sources & evidence

ORD record
ord-68a94e5bf4c749fa8a3fa55daf1ae8f0
Source dataset
uspto-grants-2010_01
Patent number
US07652013B2

Reaction notes

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