Pyridine → 6-bromo-2-(2-chlorophenyl)thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1052149Notes

Reaction equation

HRID 1052149 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([Br:7])[S:4][C:3]=1[C:8]([NH2:10])=[O:9].[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=O.N1C=CC=CC=1>CN(C)C1C=CN=CC=1.CN(C)C=O>[Br:7][C:5]1[S:4][C:3]2[C:8](=[O:9])[NH:10][C:14]([C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[Cl:11])=[N:1][C:2]=2[CH:6]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 691102-Chlorobenzoyl chlorideHCID 219758623-Amino-5-bromothiophene-2-carboxamide

Product 1

HCID 1363339036-bromo-2-(2-chlorophenyl)thieno[3,2-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-amino-5-bromothiophene-2-carboxamide (100 mg), 2-chlorobenzoylchloride (57 μL), N,N-dimethylpyridin-4-amine (55 mg), pyridine (1.0 mL) and N,N-dimethylformamide (2.0 mL) was stirred at 70° C. for 1.5 hr. The reaction system was concentrated under reduced pressure, 2M aqueous sodium hydroxide solution was added to the residue, and the mixture was heated to 120° C. After 1 hr, insoluble material was removed by filtration, and the filtrate was neutralized with 1M hydrochloric acid. The precipitate was collected by filtration and washed with water to give the title compound (120 mg) as a dark orange solid.

Workup

  1. concentrationThe reaction system was concentrated under reduced pressure, 2M aqueous sodium hydroxide solution
  2. additionwas added to the residue
  3. temperaturethe mixture was heated to 120° C
  4. waitAfter 1 hr
  5. custominsoluble material was removed by filtration
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-19e1b45b7ef34a9ebec17cc103b19d3d
Source dataset
uspto-grants-2016_07
Patent number
US09388195B2

Reaction notes

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