Sodium Hydroxide → HCID 19081762, compound

HRID 963384Notes

Reaction equation

HRID 963384 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[C:16]([C:20]3[C:25]([O:26][CH3:27])=[C:24]([O:28][CH3:29])[CH:23]=[C:22]([CH2:30][C:31]4[C:32]([NH2:38])=[N:33][C:34]([NH2:37])=[N:35][CH:36]=4)[CH:21]=3)[CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.[OH-].[Na+]>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[CH:15]=[C:16]([C:20]3[C:25]([O:26][CH3:27])=[C:24]([O:28][CH3:29])[CH:23]=[C:22]([CH2:30][C:31]4[C:32]([NH2:38])=[N:33][C:34]([NH2:37])=[N:35][CH:36]=4)[CH:21]=3)[CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:11])=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19081672HCID 19081672, compound

Product 1

HCID 19081762HCID 19081762, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

322 mg of 5-(3'-(4-nitrobenzene-sulphonylamino)-5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamine (Example 4f)) are dissolved in 15 ml of glacial acetic acid and treated portionwise with 650 mg of iron powder. The mixture is stirred at room temperature for 2 hrs. Subsequently, it is poured on to ice-water, made alkaline with dilute sodium hydroxide solution and filtered. The residue and the aqueous phase are washed with ethyl acetate; the combined organic phases are dried, evaporated and the residue is chromatographed on silica gel. Eluent: methylene chloride/methanol/conc. ammonia 90:10:1. 230 mg (76%) of 5-(3'-(4-aminobenzene-sulphonylamino)-5,6-dimethoxy-biphenyl-3-ylmethyl)-pyrimidine-2,4-diamine are isolated as a yellowish solid. M.p. 223°-226°.

Workup

  1. filtrationfiltered
  2. washThe residue and the aqueous phase are washed with ethyl acetate
  3. customthe combined organic phases are dried
  4. customevaporated
  5. customthe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-31850f2c7426486cb01b584ceb083a98
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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