Water → HCID 54540276, compound

HRID 2379901Notes

Reaction equation

HRID 2379901 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:33]1[N:41]=[CH:40][N:39]=[C:38]2[C:34]=1[NH:35][CH:36]=[N:37]2.C(NC(C)C)(C)C.O>C(#N)C>[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([C:33]3[N:41]=[CH:40][N:39]=[C:38]4[C:34]=3[NH:35][CH:36]=[N:37]4)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[NH:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 53592776-ChloropurineHCID 10048624N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-heptanamine

Product 1

HCID 54540276HCID 54540276, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-heptanamine (5.30 g, 12.2 mmol), 6-chloropurine (1.90 g, 12.3 mmol), and diisopropylamine (3.00 mL, 17.2 mmol) in acetonitrile (50 mL) was heated to mild reflux for 18 hours, and then cooled and poured into water (200 mL). This was extracted with methylene chloride (2×200 mL), and the extracts were combined, dried over anhydrous potassium carbonate, filtered and evaporated. The residue was separated by flash chromatography (ethyl acetate) to afford the title product as a solid, m.p. 58°-60° C. 1H NMR (CDCl3): 10.66 (2H, br s); 8.30 (1H, s); 7.83 (1H, s); 7.67-7.18 (10H, m); 4.10 (4H, br); 3.08 (2H, t, J=7.1 Hz); 1.80-1.20 (16 H, m); 0.89 (3H, t, J=6.6 Hz). High-resolution mass spectrum: calc. for C32H39N7S 554.3066, obs. 554.3053, diff. 2.3 ppm.

Workup

  1. temperatureto mild reflux for 18 hours
  2. temperaturecooled
  3. extractionThis was extracted with methylene chloride (2×200 mL)
  4. dry with materialdried over anhydrous potassium carbonate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was separated by flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-433d5464c1e84b61ac996f213e290aba
Source dataset
uspto-grants-1994_11
Patent number
US05364875

Reaction notes

Loading…