Dimethylformamide → HCID 67280597, compound

HRID 1694706Notes

Reaction equation

HRID 1694706 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[N:6][C:7](CN)=[N:8][CH:9]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14].[CH3:17][N:18](C=O)C>>[Br:3][C:4]1[CH:9]=[N:8][C:7]([N:18]([CH3:17])[S:13]([CH3:12])(=[O:15])=[O:14])=[N:6][CH:5]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 529878541-(5-Bromopyrimidin-2-yl)methanamine

Product 1

HCID 67280597HCID 67280597, compound

Procedure

Sodium hydride (0.22 g, 60% in oil) was added to a solution of (5-bromopyrimidin-2-yl)methylamine (0.85 g) in DMF (10 ml) at 0° C. and stirred for 30 min. Methanesulphonyl chloride (0.62 g) was added dropwise, the mixture warmed to RT and stirred for a further 2 h. The reaction was quenched with water and then extracted with EtOAc. The organics were washed with water, dried, and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 1% methanol/DCM. Yield 0.42 g

Workup

  1. stirringstirred for a further 2 h
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. washThe organics were washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was purified by chromatography on silica eluting with 1% methanol/DCM

Sources & evidence

ORD record
ord-db710433c9c6419ea4cfd8b71554b4e3
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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