(4,6-Dibromopyrimidin-2-yl)-methylamine → (4-Bromo-6-phenylsulphanylpyrimidin-2-yl)-methylamine

HRID 1603545Notes

Reaction equation

HRID 1603545 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](Br)[N:5]=[C:4]([NH:9][CH3:10])[N:3]=1.[Na].[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN1CCCC1=O>[Br:1][C:2]1[CH:7]=[C:6]([S:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:5]=[C:4]([NH:9][CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 19605496(4,6-Dibromopyrimidin-2-yl)-methylamineHCID 66586497Sodium benzenethiol

Product 1

HCID 19605540(4-Bromo-6-phenylsulphanylpyrimidin-2-yl)-methylamineYield 65.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

0.33 g (0.00124 mol) of (4,6-dibromopyrimidin-2-yl)-methylamine and 0.33 g (0.00248 mol) of thiophenol sodium salt were stirred in 15 ml of 1-methyl-2-pyrrolidone at 120° C. for 4 hrs. The solvent was removed and the residue was partitioned between water and diethyl ether. The ether phase was washed with sat. sodium chloride solution and dried over MgSO4. After filtration and removal of the solvent the residue was chromatographed on silica gel with diethyl ether/hexane 1:3 and subsequently dried in a high vacuum. There was obtained 0.24 g (65%) of (4-bromo-6-phenylsulphanylpyrimidin-2-yl)-methylamine as white crystals; m.p.: 122-124° C.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between water and diethyl ether
  3. washThe ether phase was washed with sat. sodium chloride solution
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration and removal of the solvent the residue
  6. customwas chromatographed on silica gel with diethyl ether/hexane 1:3
  7. customsubsequently dried in a high vacuum

Sources & evidence

ORD record
ord-af29d09869014e7b954582c00483183d
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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