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2-Fluoro-4-nitrophenol → 4-(2-Fluoro-4-nitrophenoxy)-6-(methylthio)thieno[3,2-d]pyrimidine

HRID 500903
Notes
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Reaction equation

HRID 500903 reaction equation
Cl[C:2]1[C:3]2[S:10][C:9]([S:11][CH3:12])=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[OH:23].C([O-])([O-])=O.[K+].[K+]>O(C1C=CC=CC=1)C1C=CC=CC=1>[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[O:23][C:2]1[C:3]2[S:10][C:9]([S:11][CH3:12])=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium CarbonateHCID 594244514-Chloro-6-(methylthio)thieno[3,2-d]pyrimidine

Product 1

HCID 594244784-(2-Fluoro-4-nitrophenoxy)-6-(methylthio)thieno[3,2-d]pyrimidineYield 88%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 280 (210 mg, 0.97 mmol), 2-fluoro-4-nitrophenol (278 mg, 1.77 mmol) and K2CO3 (560 mg, 3.54 mmol) in Ph2O (10 mL) was heated at 130° C. 60 hours, cooled to room temperature and partitioned between EtOAc and water. Organic phase was collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by flash column chromatography with a gradient elution (hexane to hexane/EtOAc, 1:1) to afford the title compound 281 (288 mg, 88% yield) as a yellowish solid. MS (m/z): 338.1(M+H) (found).

Workup

  1. temperature60 hours, cooled to room temperature
  2. custompartitioned between EtOAc and water
  3. customOrganic phase was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography with a gradient elution (hexane to hexane/EtOAc, 1:1)

Sources & evidence

ORD record
ord-fb8e88be6b074a24812d7e176aa1c03a
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07772247B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes