HCID 19605468, compound → HCID 9928029, compound

HRID 1603547Notes

Reaction equation

HRID 1603547 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[N:5]=[C:4]([NH:20][CH3:21])[N:3]=1>C(O)(=O)C.ClCCl.[Fe]>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([C:6]2[CH:7]=[C:2]([Br:1])[N:3]=[C:4]([NH:20][CH3:21])[N:5]=2)(=[O:9])=[O:10])=[CH:12][CH:13]=1

Participants

5

Reactant 1

HCID 19605468HCID 19605468, compound

Product 1

HCID 9928029HCID 9928029, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

0.40 g (0.0011 mol) of [4-bromo-6-(4-nitrobenzenesulphonyl)-pyrimidin-2-yl]-methylamine was suspended in 20 ml of acetic acid, treated with 0.40 g of iron powder and heated to 60° C. for about 4 hrs. Thereafter, the solvent was removed, the residue was digested in water and the precipitate which thereby separated was isolated. This was dissolved in dichloromethane and dried over MgSO4. After filtration and removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane 1:2 and subsequently dried in a high vacuum. There was obtained 0.25 g (68%) of [4-(4-amino-benzenesulphonyl)-6-bromopyrimidin-2-yl]-methylamine as a yellow solid; m.p.: >250° C.

Workup

  1. customThereafter, the solvent was removed
  2. customthe precipitate which thereby separated
  3. customwas isolated
  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 1:2
  7. customsubsequently dried in a high vacuum

Sources & evidence

ORD record
ord-b58e98a347d64dfcab5d225306aed871
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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