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Triethylamine → 6-bromo-2-(tetrahydrofuran-2-yl)thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1022908
Notes
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Reaction equation

HRID 1022908 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([Br:7])[S:4][C:3]=1[C:8]([NH2:10])=[O:9].C(N(CC)CC)C.[O:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[C:23](Cl)=O>O1CCCC1>[Br:7][C:5]1[S:4][C:3]2[C:8](=[O:9])[NH:10][C:23]([CH:19]3[CH2:20][CH2:21][CH2:22][O:18]3)=[N:1][C:2]=2[CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 551254Tetrahydro-2-furancarbonyl chlorideHCID 219758623-Amino-5-bromothiophene-2-carboxamide

Product 1

HCID 1363339136-bromo-2-(tetrahydrofuran-2-yl)thieno[3,2-d]pyrimidin-4(3H)-oneYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-amino-5-bromothiophene-2-carboxamide (120 mg) produced in Example 1, step D, triethylamine (0.083 mL) and tetrahydrofuran (3.0 mL) was added tetrahydrofuran-2-carbonylchloride (80 mg) with stirring at room temperature. The reaction mixture was stirred for 10 min, and the reaction system was concentrated under reduced pressure. 2M Aqueous sodium hydroxide solution (1.0 mL) was added to the residue, and the mixture was stirred with heating at 120° C. for 2 hr. The mixture was extracted with ethyl acetate, washed with brine and dried over anhydrous sodium sulfate. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (160 mg) as a pale-yellow solid.

Workup

  1. stirringThe reaction mixture was stirred for 10 min
  2. concentrationthe reaction system was concentrated under reduced pressure
  3. addition2M Aqueous sodium hydroxide solution (1.0 mL) was added to the residue
  4. stirringthe mixture was stirred
  5. temperaturewith heating at 120° C. for 2 hr
  6. extractionThe mixture was extracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customInsoluble material was removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-35f6135897824026a5ff772480de33ba
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722660B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes