Phosphorus oxychloride → 1-(4-Bromophenyl)-2-chloro-9-methyl-1,9-dihydro-6H-purin-6-one

HRID 408835Notes

Reaction equation

HRID 408835 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17](=[O:18])[C:16]3[N:15]=[CH:14][N:13]([CH3:19])[C:12]=3[N:11]=[C:10]2S)=[CH:5][CH:4]=1.O=P(Cl)(Cl)[Cl:23]>>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17](=[O:18])[C:16]3[N:15]=[CH:14][N:13]([CH3:19])[C:12]=3[N:11]=[C:10]2[Cl:23])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178478927HCID 178478927, compound

Product 1

HCID 576141521-(4-Bromophenyl)-2-chloro-9-methyl-1,9-dihydro-6H-purin-6-one

Conditions

Temperature
135 °C

Procedure

1-(4-Bromophenyl)-2-mercapto-9-methyl-1,9-dihydro-6H-purin-6-one hydrochloride (2.05 g, 5.49 mmol) is added to POCl3 (87 mL) and the resulting solution is refluxed at 135° C. for 38 h. Most volatiles are removed under vacuum and the residual solvents are co-evaporated with toluene (50 mL×3). The resulting dark solid is dissolved in CH2Cl2 (300 mL), washed with saturated NaHCO3 solution (100 mL×5), brine (50 mL×2), and dried over MgSO4. After removing solvent in vacuo, silica gel column chromatography (EtOAc:hexanes=50:50) gives the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3) 7.51 (1H, s), 7.67 (2H, d), 7.14 (2H, d), 3.83 (3H, s); m/z (ES+) 340.90 (M+).

Workup

  1. customMost volatiles are removed under vacuum
  2. dissolutionThe resulting dark solid is dissolved in CH2Cl2 (300 mL)
  3. washwashed with saturated NaHCO3 solution (100 mL×5), brine (50 mL×2)
  4. dry with materialdried over MgSO4
  5. customAfter removing solvent in vacuo, silica gel column chromatography (EtOAc:hexanes=50:50)

Sources & evidence

ORD record
ord-f7bfff0eac0d4713a4f2c9ce1397b3b9
Source dataset
uspto-grants-2014_06
Patent number
US08759361B2

Reaction notes

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