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

HRID 1828511Notes

Reaction equation

HRID 1828511 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:36]=[CH:35][N:14]3[C:15](=[O:34])[C:16]([C:20]4[N:24]([CH2:25][C:26]5[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=5)[N:23]=[N:22][N:21]=4)=[C:17]([OH:19])[N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[C:53]1([CH3:63])[CH:58]=[CH:57][C:56]([S:59](Cl)(=[O:61])=[O:60])=[CH:55][CH:54]=1>C(Cl)Cl>[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:36]=[CH:35][N:14]3[C:15](=[O:34])[C:16]([C:20]4[N:24]([CH2:25][C:26]5[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=5)[N:23]=[N:22][N:21]=4)=[C:17]([O:19][S:59]([C:56]4[CH:57]=[CH:58][C:53]([CH3:63])=[CH:54][CH:55]=4)(=[O:61])=[O:60])[N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 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-one2×

Product 1

HCID 220635268-[2-(4-Isopropyl-1,3-thiazol-2-yl)ethyl]-2-tosyloxy-3-[(4-methoxybenzyl)tetrazol-5-yl]-4H-pyrido[1,2-a]pyrimidin-4-oneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 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(73 mg) obtained in (A) was dissolved in methylene chloride (2 ml), added with dimethylaminopyridine (5 mg), triethylamine(40 ml) and p-toluenesulfonyl chloride (83 mg) at 0° C., and then the mixture was stirred at room temperature for 6 hours. The reaction solution was directly purified by silica gel column chromatography to obtain the title compound (61 mg, 64%) as pale yellow powder.

Workup

  1. customThe reaction solution was directly purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7c248996706444d9a87b2f56d30f5889
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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