1,4'-Bipiperidine → 3-Methyl-2-[4-[6-(4-piperidinopiperidinyl)nicotinoyl]benzylthio]thieno[3,2-d]pyrimidin-4(3H)-one hydrochloride

HRID 1291348Notes

Reaction equation

HRID 1291348 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([C:8]2[CH:26]=[CH:25][C:11]([CH2:12][S:13][C:14]3[N:15]([CH3:24])[C:16](=[O:23])[C:17]4[S:22][CH:21]=[CH:20][C:18]=4[N:19]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][N:3]=1.[N:29]1([CH:35]2[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>N1C=CC=CC=1>[ClH:1].[CH3:24][N:15]1[C:16](=[O:23])[C:17]2[S:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:14]1[S:13][CH2:12][C:11]1[CH:25]=[CH:26][C:8]([C:6](=[O:7])[C:5]2[CH:27]=[CH:28][C:2]([N:38]3[CH2:39][CH2:40][CH:35]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)[CH2:36][CH2:37]3)=[N:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 786071,4'-BipiperidineHCID 189187982-[4-(6-Chloronicotinoyl)benzylthio]-3-methylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 189192833-Methyl-2-[4-[6-(4-piperidinopiperidinyl)nicotinoyl]benzylthio]thieno[3,2-d]pyrimidin-4(3H)-one hydrochlorideYield 62.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-[4-(6-chloronicotinoyl]benzylthio]-3-methylthieno[3,2-d]pyrimidin-4(3H)-one (427 mg) and 4-piperidinopiperidine (202 mg) in pyridine (10 ml) was stirred at 80° C. for 10 hours. This reaction mixture was concentrated, the residue was dissolved in chloroform, and the solution was washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (chloroform: methanol: aqueous ammonia=50:1:0.1) and treated with HCl/ethyl acetate for conversion to hydrochloride to provide the title compound as colorless solid (373 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in chloroform
  3. washthe solution was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (chloroform: methanol: aqueous ammonia=50:1:0.1)
  7. additiontreated with HCl/ethyl acetate for conversion to hydrochloride

Sources & evidence

ORD record
ord-abe6b376ec6e42ebb6d54766e2f5a4c8
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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