2,4-Difluoronitrobenzene → HCID 68157451, compound

HRID 243152Notes

Reaction equation

HRID 243152 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.CC(C)([O-])C.[K+].F[C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23]>C1COCC1>[F:21][C:19]1[CH:18]=[CH:17][C:16]([N+:22]([O-:24])=[O:23])=[C:15]([NH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][N:3]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 689584-AminopyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 68157451HCID 68157451, compoundYield 12.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 4-aminopyrimidine (1.0 g, 10.52 mmol) in THF (40 ml) at 0° C. under nitrogen was added potassium tert-butoxide (2.46 g, 22 mmol). After stirring for 5 min 2,4-difluoronitrobenzene (1.672 g, 10.52 mmol) was added dropwise. The reaction was stirred for 1 h at 0° C. then at 20° C. for 1 h, then quenched with 5% citric acid to give a pH of 5. The mixture was extracted with EtOAc (150 mL), dried (Na2SO4) and evaporated to an orange gum. This was purified by column chromatography (Si—PCC, gradient 0-5% MeOH in DCM to give the title compound as a yellow solid, (0.31 g, 12%). LCMS (Method B): RT=2.16 min, [M+H]+=234.91

Workup

  1. additionwas added dropwise
  2. waitat 20° C. for 1 h
  3. customquenched with 5% citric acid
  4. customto give a pH of 5
  5. extractionThe mixture was extracted with EtOAc (150 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated to an orange gum
  8. customThis was purified by column chromatography (Si—PCC, gradient 0-5% MeOH in DCM

Sources & evidence

ORD record
ord-71eba2fc28b84ea7b56d3ba9e8a168a3
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…