Hydrogen Peroxide → HCID 5329433, compound

HRID 968252Notes

Reaction equation

HRID 968252 reaction equation
[C:1]1([C:7]2[N:8]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:19]4[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=4)[N:13]=3)[CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:25]O>C(Cl)Cl>[O-:25][N+:21]1[CH:22]=[CH:23][CH:24]=[C:19]([NH:18][C:14]2[N:13]=[C:12]([N:8]3[CH:9]=[CH:10][N:11]=[C:7]3[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:17]=[CH:16][N:15]=2)[CH:20]=1

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 5329431HCID 5329431, compound

Product 1

HCID 5329433HCID 5329433, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-phenyl-1H-imidazol-1-yl)-N-pyridin-3-ylpyrimidin-2-amine (3-3, 0.17 mmol) in CH2Cl2 (1 mL) was added MeReO3 (1 mg) then 30% H2O2 (0.05 mL) with vigorous stirring at room temperature. After 18 hrours additional MeReO3 (1 mg) and 30% H2O2 (0.05 mL) were added. After 18 hours the mixture was concentrated. Purification by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA) gave the title compound as a tan solid after trituration with Et2O. 1H-NMR (500 MHz, d6-DMSO) δ 10.38 (s, 1H), 8.68 (d, J=5.13 Hz, 1H), 8.57 (s, 1H), 7.99 (s, 1H), 7.87 (d, J=5.86 Hz, 1H), 7.55 (m, 6H), 7.27 (bs, 1H), 7.20 (s, 1H), 6.86 (d, J=4.64 Hz, 1H).

Workup

  1. concentrationAfter 18 hours the mixture was concentrated
  2. customPurification by reverse phase HPLC (5-100% CH3CN/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-2558440a6ffd45fa963c02d46bacecbf
Source dataset
uspto-grants-2005_10
Patent number
US06958340B2

Reaction notes

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