2-Propylimidazole → 2-Chloro-6-(2-propylimidazol-1-yl)purine

HRID 2264864Notes

Reaction equation

HRID 2264864 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.[CH2:12]([C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)[CH2:13][CH3:14]>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([N:16]2[CH:17]=[CH:18][N:19]=[C:15]2[CH2:12][CH2:13][CH3:14])[N:3]=1

Participants

4

Reactant 2

HCID 1626172-PropylimidazoleHCID 53244122,6-Dichloropurine

Product 1

HCID 115579952-Chloro-6-(2-propylimidazol-1-yl)purineYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

2,6-Dichloropurine (0.38 g, 2 mmol) and 2-propylimidazole (1.32 g, 12 mmol) were dissolved in freshly distilled DMF (10 mL), and the mixture was stirred at 65° C. for 20 h. Volatiles were evaporated in vacuo, and the residue was dissolved in 0.1 N NaOH/H2O//CH2Cl2 (100 mL/50 mL). The organic phase was extracted with 0.1 N NaOH/H2O (3×50 mL). The combined aqueous phase was washed with CH2Cl2 (2×50 mL) and neutralized with CO2. The precipitated solid was filtered and washed (H2O) to give 2-chloro-6-(2-propylimidazol-1-yl)purine (0.38 g, 72%): mp 224.5-225° C.; UV (MeOH) max 215, 288 nm (∈ 25 800, 16 700), min 332, 241 nm (∈ 2500, 4500); 1H NMR (500 MHz, DMSO-d6) δ 14.04 (br s, 1H), 8.69 (s, 1H), 8.43 (s, 1H), 7.06 (s, 1H,), 3.12 (t, J=7.5 Hz, 2H), 1.72 (sext, J=7.3 Hz, 2H), 0.95 (t, J=7.3 Hz, 3H); 13C NMR (125 MHz, DMSO-d6) δ 157.3, 151.7, 150.2, 147.2, 146.6, 128.9, 122.5, 121.1, 32.4, 21.5, 14.5; HRMS m/z 262.0723 (M+[C11H11ClN6]=262.0734). Anal. Calcd for C11H11ClN6: C, 50.29; H, 4.22; N, 31.99. Found: C, 50.02; H, 4.28; N, 31.64.

Workup

  1. customVolatiles were evaporated in vacuo
  2. dissolutionthe residue was dissolved in 0.1 N NaOH/H2O//CH2Cl2 (100 mL/50 mL)
  3. extractionThe organic phase was extracted with 0.1 N NaOH/H2O (3×50 mL)
  4. washThe combined aqueous phase was washed with CH2Cl2 (2×50 mL)
  5. filtrationThe precipitated solid was filtered
  6. washwashed (H2O)

Sources & evidence

ORD record
ord-bef833257f184d6abb0a1343c6f9fb9f
Source dataset
uspto-grants-2010_12
Patent number
US07855285B2

Reaction notes

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