Stannous chloride dihydrate → 4-(Benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)aniline

HRID 452329Notes

Reaction equation

HRID 452329 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]3[C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=[C:12]3[N:11]=2)=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl>C(O)C>[N:11]1[C:12]2[N:13]([C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)[CH:14]=[CH:15][C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 583625512-(4-Nitrophenyl)benzo[4,5]imidazo[1,2-a]pyrimidine

Product 1

HCID 583624164-(Benzo[4,5]imidazo[1,2-a]pyrimidin-2-yl)anilineYield 67.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(4-nitrophenyl)benzo[4,5]imidazo[1,2-a]pyrimidine (58 mg, 0.20 mmol) in ethanol (3 mL) was added SnCl2.2H2O (361 mg, 1.6 mmol). The solution was refluxed for 1.5 hours and then the volatiles were removed under vacuum. The residue was dissolved in DCM, washed with 1 N NaOH, and then H2O. The DCM layer was dried with MgSO4. The crude product was purified on flash chromatography (silica gel, 5% MeOH/DCM) to provide T518 as a yellow solid (35 mg, 67%). 1H NMR (400 MHz, DMSO-d6) δ 5.94 (s, 2H), 6.70 (m, 2H), 7.34 (m, 1H), 7.47 (m, 1H), 7.61 (d, J=7.6 Hz, 1H), 7.75 (m, 1H), 8.08 (m, 2H), 8.21 (m, 1H), 9.34 (d, J=7.6 Hz, 1H). MS (ESI): 261.1 (M+H+).

Workup

  1. temperatureThe solution was refluxed for 1.5 hours
  2. customthe volatiles were removed under vacuum
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with 1 N NaOH
  5. dry with materialThe DCM layer was dried with MgSO4
  6. customThe crude product was purified on flash chromatography (silica gel, 5% MeOH/DCM)

Sources & evidence

ORD record
ord-d27b8d0a9db249b2bcab8433555d29ba
Source dataset
uspto-grants-2013_07
Patent number
US08491869B2

Reaction notes

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