Potassium Carbonate → 2-[(2-Nitrophenyl)sulfanyl]pyrimidine

HRID 1642263Notes

Reaction equation

HRID 1642263 reaction equation
[SH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.F[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N+:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[S:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 178418793HCID 178418793, compound

Product 1

HCID 575502792-[(2-Nitrophenyl)sulfanyl]pyrimidineYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2 mercaptopyrimidine (2.00 g, 17.8 mmol), 1-fluoro-2-nitrobenzene (2.50 g, 17.8 mmol) and potassium carbonate (2.46 g, 17.8 mmol) in DMF (15 mL) was stirred under reflux for 2 h. After removal of DMF, the residue was dissolved in DCM and washed with NaOH (5%, 3×20 mL) and brine. The organic layer was dried (MgSO4), filtered and evaporated to give 2-(2-nitro-phenylsulfanyl)-pyrimidine (3.45 g, 83%) as a yellow solid which was used in the next step without further purification. LC/MS (APCI) tr=3.66 min, m/z 379.28 (39), 233.98 (M++H, 100). HPLC tr=2.22 min (99.67%) 1H NMR (270 MHz, CDCl3) δ 7.03 (1H, t, J=4.7 Hz, Pyrimidine-H), 7.51-7.64 (2H, m, ArH), 7.80 (1H, dd, J=7.7, 1.5 Hz, ArH), 8.03 (1H, dd, J=7.7, 2.0 Hz, ArH) and 8.48 (2H, d, J=4.7 Hz, Pyrimidine-H).

Workup

  1. temperatureunder reflux for 2 h
  2. customAfter removal of DMF
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with NaOH (5%, 3×20 mL) and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-cd36defe4ce546e9935a58eb7aa1ad03
Source dataset
uspto-grants-2012_02
Patent number
US08119627B2

Reaction notes

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