1-(4-(5-Bromopyrimidin-2-ylsulfanyl)phenyl)-3-(2-nitrobenzoyl)urea → 1-(2-Aminobenzoyl)-3-(4-(5-bromopyrimidin-2-ylsulfanyl)phenyl)urea

HRID 736330Notes

Reaction equation

HRID 736330 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([S:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]([NH:18][C:19](=[O:29])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N+:26]([O-])=O)=[O:17])=[CH:11][CH:10]=2)=[N:6][CH:7]=1>CC(O)=O.O.[Fe]>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:19]([NH:18][C:16]([NH:15][C:12]1[CH:11]=[CH:10][C:9]([S:8][C:5]2[N:6]=[CH:7][C:2]([Br:1])=[CH:3][N:4]=2)=[CH:14][CH:13]=1)=[O:17])=[O:29]

Participants

5

Reactant 1

HCID 113174691-(4-(5-Bromopyrimidin-2-ylsulfanyl)phenyl)-3-(2-nitrobenzoyl)urea

Product 1

HCID 113627701-(2-Aminobenzoyl)-3-(4-(5-bromopyrimidin-2-ylsulfanyl)phenyl)ureaYield 62%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Iron powder (1.77 g, 31.63 mmol) was added in portions to a mixture of 6n (3 g, 6.32 mmol) in AcOH (90 mL) at 80° C. The reaction mixture was refluxed for 30 min and then cooled to room temperature and diluted with water. The precipitated solid was collected by filtration. The solid was dissolved in an excess of ethyl acetate and filtered. The filtrate was dried and concentrated to give a residue that was purified by silica gel flash column chromatography (ethyl acetate-hexane 2:3) to give 7d, yield 62%. 1H NMR (400 MHz, DMSO-d6): δ 11.92 (br, s, 1H), 10.73 (br, s, 1H), 8.75 (s, 2H), 7.68 (m, 2H), 7.57 (m, 2H), 7.25 (m, 1H), 6.79 (m, 1H), 6.59 (m 2H); EI-MS m/z 443 [M]+, 445 [M+2]+; HRMS calculated for C18H12BrN5O2SNa [M+Na]+: 465.9943, found: 465.9938. Anal. (C18H14BrN5O2S) C, H, N.

Workup

  1. temperatureThe reaction mixture was refluxed for 30 min
  2. filtrationThe precipitated solid was collected by filtration
  3. dissolutionThe solid was dissolved in an excess of ethyl acetate
  4. filtrationfiltered
  5. customThe filtrate was dried
  6. concentrationconcentrated
  7. customto give a residue that
  8. customwas purified by silica gel flash column chromatography (ethyl acetate-hexane 2:3)

Sources & evidence

ORD record
ord-132a801b52ba43c1b4c269763f160c64
Source dataset
uspto-grants-2009_09
Patent number
US07595326B2

Reaction notes

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