Bromine → HCID 22729463, compound

HRID 2085420Notes

Reaction equation

HRID 2085420 reaction equation
[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([CH:10]3[N:15]([C:16]([O:18][C:19]4[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=4)=[O:17])[C:14]([O:28]C)=[N:13][C:12]([CH3:30])=[C:11]3[C:31]([O:33][CH3:34])=[O:32])[CH:8]=[CH:9][C:2]=12.[Br:35]Br>C(Cl)(Cl)Cl>[N:1]1[O:5][N:4]=[C:3]2[CH:6]=[C:7]([CH:10]3[N:15]([C:16]([O:18][C:19]4[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=4)=[O:17])[C:14](=[O:28])[NH:13][C:12]([CH2:30][Br:35])=[C:11]3[C:31]([O:33][CH3:34])=[O:32])[CH:8]=[CH:9][C:2]=12

Participants

4

Reactant 2

HCID 24408BromineHCID 10624096HCID 10624096, compound

Product 1

HCID 22729463HCID 22729463, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Into a well-stirred solution of 6-(benzofurazan-5-yl)-1,6-dihydro-2-methoxy-5-methoxycarbonyl-4-methyl-1-[(4-nitrophenyl-oxy)carbonyl]pyrimidine (0.310 mmol, 0.140 g) in 1.5 mL of chloroform was added a solution of bromine (0.310 mmol, 0.020 mL) in 1.5 mL of chloroform at 0° C. and the solution was allowed to attain room temperature over 1.5 h. The solvent was removed in vacuo and the residue was again dissolved in CHCl3 (10 mL) and washed with brine. The organic layer was separated, dried over Na2SO4, filtered and the solvent was removed in vacuo to obtain 0.15 g (88% yield) of 6-(benzofurazan-5-yl)-1,6-dihydro-2-oxo-5-methoxycarbonyl-4-bromomethyl-1-[(4-nitrophenyl-oxy)carbonyl]pyrimidine as a yellow foam. The crude product was used in the next step without purification. 1H NMR (CDCl3) δ 3.79 (s, 3 H), 4.72 (ABq, 2 H), 6.47 (s, 1 H), 7.37 (d, J=9.1 Hz, 2 H), 7.51 (d, J=7.8 Hz, 1 H), 7.80 (s, 1 H), 7.92 (d, J=9.1 Hz, 1 H), 8.30 (d, J=9.1 Hz, 2 H).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was again dissolved in CHCl3 (10 mL)
  3. washwashed with brine
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d2ff133a0c544b7f80310f1a61d6324a
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

Loading…