4-[2-(4-Isopropyl-1,3-thiazol-2-yl)ethyl]-2-aminopyridine → 8-[2-(4-Isopropyl-1,3-thiazol-2-yl)ethyl]-2-hydroxy-3-[(4-methoxybenzyl)tetrazol-5-yl]-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1828510Notes

Reaction equation

HRID 1828510 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH2:17])[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].[CH3:18][O:19][C:20]1[CH:42]=[CH:41][C:23]([CH2:24][N:25]2[C:29]([CH:30]([C:36](OCC)=[O:37])[C:31](OCC)=[O:32])=[N:28][N:27]=[N:26]2)=[CH:22][CH:21]=1>BrC1C=CC=CC=1>[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]3[C:31](=[O:32])[C:30]([C:29]4[N:25]([CH2:24][C:23]5[CH:41]=[CH:42][C:20]([O:19][CH3:18])=[CH:21][CH:22]=5)[N:26]=[N:27][N:28]=4)=[C:36]([OH:37])[N:17]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 220636524-[2-(4-Isopropyl-1,3-thiazol-2-yl)ethyl]-2-aminopyridineHCID 22063755Diethyl 2-[1-(4-methoxybenzyl)tetrazol-5-yl]malonate

Product 1

HCID 1357244388-[2-(4-Isopropyl-1,3-thiazol-2-yl)ethyl]-2-hydroxy-3-[(4-methoxybenzyl)tetrazol-5-yl]-4H-pyrido[1,2-a]pyrimidin-4-oneYield 71.7%

Reagents, catalysts & solvents 1

HCID 7961BromobenzeneSolvent

Procedure

4-[2-(4-Isopropyl-1,3-thiazol-2-yl)ethyl]-2-aminopyridine (50 mg) and diethyl 2-[1-(4-methoxybenzyl)tetrazol-5-yl]malonate (141 mg) were heated to 150° C. in bromobenzene with stirring for 4 hours. After the solvent was evaporated, the residue was purified by silica gel column chromatography to obtain the title compound (73 mg) as cream solid.

Workup

  1. customAfter the solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e16a421f5eee48ed99d233754d116ddb
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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