Potassium Carbonate → HCID 18956336, compound

HRID 2379902Notes

Reaction equation

HRID 2379902 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([SH:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[SH:23][C:24]1[N:32]=[CH:31][N:30]=[C:29]2[C:25]=1[NH:26][CH:27]=[N:28]2.C(=O)([O-])[O-].[K+].[K+].O1[CH2:43][CH2:42][CH2:41][CH2:40]1.CN(C)C=O>C(OCC)(=O)C>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[C:11]([S:22][CH2:40][C:41]3[CH:5]=[C:6]([CH:7]=[CH:43][CH:42]=3)[CH2:9][S:23][C:24]3[N:32]=[CH:31][N:30]=[C:29]4[C:25]=3[NH:26][CH:27]=[N:28]4)[NH:10][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 21974620tetrahydrofuran N,N-dimethylformamideHCID 178489021HCID 178489021, compoundHCID 178527888HCID 178527888, compound

Product 1

HCID 18956336HCID 18956336, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,5-bis(4-methoxyphenyl)-2-mercapto-1H-imidazole (3.00 g, 9.60 mmol), 6-mercaptopurine (1.63 g, 9.60 mmol) a,a'-dibromoxylene (2.54 g, 9.60 mmol), and potassium carbonate (3.32 g, 24.0 mmol) and in 5:1 tetrahydrofuran-dimethylformamide (12 mL) was heated to reflux for 20 hours, then cooled. It was poured into ethyl acetate (150 mL), and washed with water (4×150 mL). The aqueous phases were back-extracted in sequence with ethyl acetate. The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residual oil was separated by flash chromatography (ethyl acetate) to afford the title product as a crystalline solid, m.p. 129°-130° C. (1.64 g, 2.89 mmol, 30%). 1H NMR (CDCl3): 8.63 (1H, s); 8.02 (1H, s); 7.30 (4H, d, J=8.8 Hz); 7.23 (1H, s); 7.16 (1H, d, J=8 Hz); 6.99 (1H, t, J=8 Hz); 6.81 (1H, d, J=8 Hz); 6.71 (4H, d, J=8.8 Hz); 4.44 (2H, s); 4.02 (2H, s); 3.69 (6H, s). Elemental analysis: calculated C 63.58, H 4.62, N 14.83; observed C 63.25, H 4.55, N 14.72.

Workup

  1. temperatureto reflux for 20 hours
  2. temperaturecooled
  3. washwashed with water (4×150 mL)
  4. extractionThe aqueous phases were back-extracted in sequence with ethyl acetate
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residual oil was separated by flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-5ddb3fb28067433098e2060b73156089
Source dataset
uspto-grants-1994_11
Patent number
US05364875

Reaction notes

Loading…