Trimethylsilyl iodide → HCID 118023603, compound

HRID 522689Notes

Reaction equation

HRID 522689 reaction equation
[F:1][C:2]([F:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][N:12](C([O-])=O)[CH2:11][CH2:10]2)=[N:7][CH:8]=1.I[Si](C)(C)C>C(Cl)(Cl)Cl>[F:24][C:2]([F:1])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 131735540HCID 131735540, compound

Product 1

HCID 118023603HCID 118023603, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-(5-(difluoro(phenyl)methyl)pyrimidin-2-yl)piperazine-1-carboxylate (180 mg, 0.42 mmol) in chloroform (5.0 mL) was added iodotrimethylsilane (0.8 mL) and the mixture was stirred at room temperature for 0.5 h. The reaction was quenched by methanol (1.0 mL), followed by the addition of 2 N HCl/dioxane (2.0 mL) and evaporated to dryness. The residue was dissolved in methanol (1.5 mL) and dropwise added into acetone (100 mL). The solid was collected by filtration and washed with acetone (10 mL) to afford crude 5-(difluoro(phenyl)methyl)-2-(piperazin-1-yl)pyrimidine (88 mg) as a yellow solid. MS (ES+) C15H16F2N4 requires: 290, found: 291 [M+H]+.

Workup

  1. customThe reaction was quenched by methanol (1.0 mL)
  2. additionfollowed by the addition of 2 N HCl/dioxane (2.0 mL)
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in methanol (1.5 mL)
  5. additiondropwise added into acetone (100 mL)
  6. filtrationThe solid was collected by filtration
  7. washwashed with acetone (10 mL)

Sources & evidence

ORD record
ord-2539cdfa8bf64ddb934dbb5243bd6ee1
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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