2-Aminopyrimidine → HCID 68156882, compound

HRID 243161Notes

Reaction equation

HRID 243161 reaction equation
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[NH2:11][C:12]1[N:17]=[CH:16][CH:15]=[CH:14][N:13]=1.F[C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27]>O1CCCC1>[F:25][C:23]1[CH:22]=[CH:21][C:20]([N+:26]([O-:28])=[O:27])=[C:19]([NH:11][C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:24]=1

Participants

5

Reactant 3

HCID 79782-AminopyrimidineHCID 679672,4-DifluoronitrobenzeneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 68156882HCID 68156882, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiHMDS (1.0 M in tetrahydrofuran, 27.4 ml, 27.4 mmol) was added to 2-aminopyrimidine (1.43 g, 15.0 mmol) in tetrahydrofuran (50.0 ml) and stirred for 10 min. 2,4-Difluoronitrobenzene (1.50 ml, 13.7 mmol) was added and the reaction stirred for a further 15 min. The reaction mixture was quenched with water then poured into sodium bicarbonate (dilute aqueous) and the aqueous layer extracted with EtOAc (×3). The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The product was purified by chromatography (SiO2, 0-100% EtOAc/cyclohexane) to yield the title compound (800 mg, 3.42 mmol, 25%). 1H NMR (CDCl3, 400 MHz): δ 8.94 (1H, dd, J 12.3, 2.4 Hz), 8.62 (2H, d, J=4.8 Hz), 8.36 (1H, dd, J 9.4, 6.1 Hz), 7.08 (1H, t, J=4.8 Hz), 6.88 (1H, ddd, J 9.6, 7.2, 2.8 Hz).

Workup

  1. stirringthe reaction stirred for a further 15 min
  2. customThe reaction mixture was quenched with water
  3. additionthen poured into sodium bicarbonate (dilute aqueous)
  4. extractionthe aqueous layer extracted with EtOAc (×3)
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by chromatography (SiO2, 0-100% EtOAc/cyclohexane)

Sources & evidence

ORD record
ord-9b04834cf8694f8cb30db66416dff108
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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