HCID 118023371, compound → Tert-butyl 4-(5-(1-(4-fluorophenyl)vinyl)pyrimidin-2-yl)piperazine-1-carboxylate

HRID 1498857Notes

Reaction equation

HRID 1498857 reaction equation
[Li][CH2:2]CCC.[F:6][C:7]1[CH:33]=[CH:32][C:10]([C:11]([C:13]2[CH:14]=[N:15][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[N:17][CH:18]=2)=O)=[CH:9][CH:8]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[F:6][C:7]1[CH:33]=[CH:32][C:10]([C:11]([C:13]2[CH:14]=[N:15][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[N:17][CH:18]=2)=[CH2:2])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 118023371HCID 118023371, compoundHCID 178418339Butyllithium

Product 1

HCID 118022879Tert-butyl 4-(5-(1-(4-fluorophenyl)vinyl)pyrimidin-2-yl)piperazine-1-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of methyltriphenylphosphonium bromide (6.0 g, 16.84 mmol) in THF (40 mL) at −78° C. was dropwise added n-BuLi (2.4 M, 7.2 mL, 17.19 mmol). After stirred at −78° C. for 1 h, tert-butyl 4-(5-(4-fluorobenzoyl)pyrimidin-2-yl)piperazine-1-carboxylate (1.3 g, 3.37 mmol) was added. The reaction mixture was stirred at RT overnight. LCMS showed the reaction was completed. The reaction was quenched with aqueous NH4Cl solution and extracted with EA (2×50 mL). The organic phases were washed with H2O (3×30 mL) and brine (50 mL), dried over sodium sulfate, filtered, concentrated and purified by silica gel chromatography (PE:EA=10:1) to get the title compound as a white solid (1.2 g, 93%). MS (ES+) C21H25FN4O2 requires: 384. found: 329 [M−56+1]+.

Workup

  1. customat −78° C.
  2. stirringThe reaction mixture was stirred at RT overnight
  3. customThe reaction was quenched with aqueous NH4Cl solution
  4. extractionextracted with EA (2×50 mL)
  5. washThe organic phases were washed with H2O (3×30 mL) and brine (50 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by silica gel chromatography (PE:EA=10:1)

Sources & evidence

ORD record
ord-fc9ed9b9be584d64b552f1d3b2d7d7ba
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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