Trimethyltin chloride → 3-(Trimethylstannyl)imidazo[1,2-a]pyrimidine

HRID 1505939Notes

Reaction equation

HRID 1505939 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:5]2=[N:4][CH:3]=1.C([Mg]Cl)(C)C.Cl[Sn:17]([CH3:20])([CH3:19])[CH3:18]>O1CCCC1>[CH3:18][Sn:17]([CH3:20])([CH3:19])[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[N:10][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 27638713-Bromoimidazo(1,2-a)pyrimidineHCID 178418918HCID 178418918, compound

Product 1

HCID 582664183-(Trimethylstannyl)imidazo[1,2-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (−78° C.) solution of 3-bromoimidazo[1,2-a]pyrimidine (1.0 g, 5.1 mmol) in anhydrous tetrahydrofuran (40 mL) under an atmosphere of nitrogen was added isopropylmagnesium chloride (2.0M solution in tetrahydrofuran, 2.8 mL, 5.6 mmol) dropwise over 10 minutes. The reaction was stirred for 2 h then a solution of chlorotrimethylstannane (1.1 g, 5.6 mmol) in tetrahydrofuran (10 mL) was added dropwise over 10 minutes. The reaction mixture was stirred for 30 minutes then allowed to warm to room temperature. The reaction was quenched with water (20 mL) and extracted with DCM (2×50 mL). The combined organic layer was dried over sodium sulfate, filtered, and evaporated in vacuo to afford the title compound as an orange oil which was used without any further purification.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. customThe reaction was quenched with water (20 mL)
  3. extractionextracted with DCM (2×50 mL)
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-6d7a491daa8d46cb90f568d39c844874
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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