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

HRID 1603546Notes

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

Participants

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

customThe solvent was removed
customthe residue was partitioned in water
washThe combined organic phases were washed with sat. sodium chloride solution
dry with materialdried over MgSO4
filtrationAfter filtration and removal of the solvent the residue
customwas chromatographed on silica gel with ethyl acetate/hexane 1:9
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

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