Sodium hydride → HCID 67152688, compound

HRID 899359Notes

Reaction equation

HRID 899359 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[N:8][C:7]([Sn:10]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:6][N:5]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C1COCC1>[CH3:23][S:24]([NH:3][C:4]1[CH:9]=[N:8][C:7]([Sn:10]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:6][N:5]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 179987355-(Tributylstannyl)pyrazin-2-amine

Product 1

HCID 67152688HCID 67152688, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (60%, 20 mg) was added into a solution of 2-amino-5-(tri-n-butylstannyl)pyrazine (0.2 g) in THF (30 mL) at room temperature. After the mixture stirred at room temperature for 30 minutes, to it was added methylsulfonyl chloride (63 mg). The reaction mixture was stirred at room temperature over 8 hours. The reaction was quenched with aqueous ammonium chloride solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic extract was dried over magnesium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography to afford 2-methylsulfonylamino-5-(tri-n-butylstannyl)pyrazine (20 mg).

Workup

  1. stirringThe reaction mixture was stirred at room temperature over 8 hours
  2. customThe reaction was quenched with aqueous ammonium chloride solution
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
  5. extractionThe combined organic extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo
  9. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ca4a66f9c4104f12afe53cd4c0fd2365
Source dataset
uspto-grants-2008_04
Patent number
US07354924B2

Reaction notes

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