Sodium hydride → HCID 67281141, compound

HRID 1694718Notes

Reaction equation

HRID 1694718 reaction equation
[H-].[Na+].[CH2:3]([NH:10][C:11]1[N:16]=[CH:15][C:14]([Br:17])=[CH:13][N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>CN(C=O)C>[Br:17][C:14]1[CH:15]=[N:16][C:11]([N:10]([CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[S:19]([CH3:18])(=[O:21])=[O:20])=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 51391422-BENZYLAMINO-5-BROMOPYRIMIDINE

Product 1

HCID 67281141HCID 67281141, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.1 g, 60% disp. in oil) was added to a stirred solution of benzyl-(5-bromo-pyrimidin-2-yl)-amine (0.55 g) in DMF (8 ml) at 0° C. After 30 min methanesulphonyl chloride (0.286 g) was added and the mixture stirred at RT for 2 h then partitioned between ethyl acetate and water. The organics were separated washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with dichloromethane. Yield 0.41 g

Workup

  1. customthen partitioned between ethyl acetate and water
  2. customThe organics were separated
  3. washwashed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. customThe residue was purified by chromatography on silica eluting with dichloromethane

Sources & evidence

ORD record
ord-8ac5083582b54a5881861183c061f556
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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