Ethanol → 3-amino-5,6-dimethyl-2-[3-(4-quinolin-2-ylpiperazin-1-yl)-propylthio]-3H-thieno[2,3-d]pyrimidin-4-one

HRID 1714761Notes

Reaction equation

HRID 1714761 reaction equation
[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([CH3:13])=[C:10]([CH3:12])[S:11][C:5]=2[N:4]=[C:3]1[S-:14].[K+].NC1SC(C)=C(C)C=1C(OCC)=O.Cl[CH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:40]=2)[CH2:35][CH2:34]1.C(O)C>C(Cl)(Cl)Cl>[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([CH3:13])=[C:10]([CH3:12])[S:11][C:5]=2[N:4]=[C:3]1[S:14][CH2:30][CH2:31][CH2:32][N:33]1[CH2:38][CH2:37][N:36]([C:39]2[CH:48]=[CH:47][C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[N:40]=2)[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 702EthanolHCID 78536Ethyl 2-amino-4,5-dimethyl3-thenoateHCID 30355894-(Chloropropyl)-1-(2-quinolyl)piperazineHCID 23701453Potassium 3-amino-5,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-thiolate

Product 1

HCID 111908233-amino-5,6-dimethyl-2-[3-(4-quinolin-2-ylpiperazin-1-yl)-propylthio]-3H-thieno[2,3-d]pyrimidin-4-oneYield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 80 mg of potassium 3-amino-5,6-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-2-thiolate, which was prepared from ethyl 2-amino-4,5-dimethylthiophene-3-carboxylate; 104 mg of 2-[4-(3-chloropropyl)piperazin-1-yl]quinoline as prepared in the Step 1-1-B; and 5 ml of ethanol, was heated under reflux for 4.5 hours. After cooling off the reaction mixture, chloroform was added, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified on silica gel column chromatography (chloroform:methanol=100: 1) to provide 72 mg (50%) of 3-amino-5,6-dimethyl-2-[3-(4-quinolin-2-ylpiperazin-1-yl)-propylthio]-3H-thieno[2,3-d]pyrimidin-4-one.

Workup

  1. temperatureunder reflux for 4.5 hours
  2. additionwas added
  3. washby washing with saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified on silica gel column chromatography (chloroform:methanol=100: 1)

Sources & evidence

ORD record
ord-cc6cd19d999744c9a3292ecfedcae500
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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