Potassium Carbonate → 3-Methyl-2-[4-[4-(2-piperidinoethoxy) benzoyl]benzylthio]thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1291351Notes

Reaction equation

HRID 1291351 reaction equation
[OH: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][CH:3]=1.Cl.Cl[CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[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]([O:1][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]3)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 189189232-[4-(4-hydroxybenzoyl)benzylthio]-3-methylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 699603573-Methyl-2-[4-[4-(2-piperidinoethoxy) benzoyl]benzylthio]thieno[3,2-d]pyrimidin-4(3H)-oneYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[4-(4-hydroxybenzoyl)benzylthio]-3-methylthieno[3,2-d]pyrimidin-4(3H)-one (408 mg), 1-(2-chloroethyl) piperidine hydrochloride (202 mg) and potassium carbonate (414 mg) in DMF (10 ml) was stirred at 60° C. for 15 hours. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, and dried. Then, hydrogen chloride/ethyl acetate was added and the precipitated hydrochloride was collected by filtration and dried to provide the title compound as colorless solid (471 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customdried
  5. additionThen, hydrogen chloride/ethyl acetate was added
  6. filtrationthe precipitated hydrochloride was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-77d536820aab4b03a4d3b655d1e99a1a
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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