Sodium hydride → HCID 59278443, compound

HRID 1361234Notes

Reaction equation

HRID 1361234 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15]>C1COCC1.O>[C:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:13]([CH3:12])[S:14]([CH3:17])(=[O:16])=[O:15])[N:7]=1)#[N:9]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 97632N-MethylmethanesulfonamideHCID 2466472-Chloropyrimidine-4-carbonitrile

Product 1

HCID 59278443HCID 59278443, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloropyrimidine-4-carbonitrile (0.20 g, 1.43 mmol) in THF was 60% NaH (0.05 g, 2.00 mmol) in mineral oil. After 20 minutes, N-methylmethanesulfonamide (0.22 g, 2.00 mmol) was added. After 3 hours, the reaction was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 30% ethyl acetate in heptane. The major fractions were combined and the solvent was concentrated in vacuo to afford N-(4-cyano-pyrimidin-2-yl)-N-methyl-methanesulfonamide.

Workup

  1. waitAfter 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 30% ethyl acetate in heptane
  8. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-c303dad4250d4c6d8a523795597f1d11
Source dataset
uspto-grants-2011_02
Patent number
US07879873B2

Reaction notes

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