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

HRID 1261346Notes

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

Participants

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

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

Sources & evidence

ORD record: ord-368089bf9e954c4693d1e8196e3efc05
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470850B2

Reaction notes

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