HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

(4,6-Dibromopyrimidin-2-yl)-methylamine → [4-Bromo-6-(4-nitrophenylsulphanyl)-pyrimidin-2-yl]-methylamine

HRID 1603546
Notes
Print preview

Reaction equation

HRID 1603546 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([NH:9][CH3:10])[N:3]=1.[K].[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1)([O-:14])=[O:13]>CN1CCCC1=O>[Br:8][C:6]1[CH:7]=[C:2]([S:21][C:18]2[CH:19]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=2)[N:3]=[C:4]([NH:9][CH3:10])[N:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 19605496(4,6-Dibromopyrimidin-2-yl)-methylamineHCID 700026814Nitrothiophenol potassium salt

Product 1

HCID 19605548[4-Bromo-6-(4-nitrophenylsulphanyl)-pyrimidin-2-yl]-methylamineYield 56.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

0.70 g (0.0026 mol) of (4,6-dibromopyrimidin-2-yl)-methylamine and 0.56 g (0.0026 mol) of 4-nitrothiophenol potassium salt were dissolved in 15 ml of 1-methyl-2-pyrrolidone and stirred at 50° C. for 5 hrs. The solvent was removed and the residue was partitioned in water and ethyl acetate. The combined organic phases were 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 ethyl acetate/hexane 1:9 and subsequently dried in a high vacuum. There was obtained 0.50 g (56%) of [4-bromo-6-(4-nitrophenylsulphanyl)-pyrimidin-2-yl]-methylamine as yellow crystals; m.p.: 204-205° C.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned in water
  3. washThe combined organic phases were 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 ethyl acetate/hexane 1:9
  7. customsubsequently dried in a high vacuum

Sources & evidence

ORD record
ord-3cd8662efec04839942344a00aa271a1
Source dataset
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05990105

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes