Imidazole → HCID 11608114, compound

HRID 2264874Notes

Reaction equation

HRID 2264874 reaction equation
C([NH:20][C:21]1[NH:22][C:23](=O)[C:24]2[N:25]=[CH:26][N:27](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:28]=2[N:29]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.II.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[NH:71]1[CH:75]=[CH:74][N:73]=[CH:72]1.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[NH2:20][C:21]1[N:29]=[C:28]2[C:24]([NH:25][CH:26]=[N:27]2)=[C:23]([N:71]2[CH:75]=[CH:74][N:73]=[CH:72]2)[N:22]=1

Participants

7

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 135461120HCID 135461120, compound

Product 1

HCID 11608114HCID 11608114, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 2-N,9-bistritylguanine (1.90 g, 3 mmol), I2 (3.88 g, 15 mmol), Ph3P (3.99 g, 15 mmol) and imidazole (1.10 g, 15 mmol) was stirred in toluene (150 mL) at 95° C. for 15 min, and DIPEA (2.9 mL, 2.15 g, 16.6 mmol) was added. The mixture was stirred at 95° C. overnight. After removal of volatiles, the residue was boiled with EtOAc (3×) and filtered hot. The combined EtOAc extracts were evaporated to dryness. The residue was dissolved in TFA/H2O (9:1, 60 mL), and the solution was stirred at 0° C. for 4 h. Volatiles were evaporated in vacuo, and the residue was dissolved in 0.1 N NaOH/H2O//CH2Cl2 (100 mL/100 mL). The organic layer was extracted with 0.1 N NaOH/H2O (50 mL×2), and the aqueous phase was combined, washed [CH2Cl2 (2×50 mL)], and neutralized with CO2. Volatiles were evaporated in vacuo, and the residue was washed (H2O, CH2Cl2) to give 2-amino-6-(imidazol-1-yl)purine (0.40 g, 69%): UV (MeOH) max 222, 320 nm (∈ 29 800, 8700), min 207, 280 nm (∈ 16 100, 1500); 1H NMR (500 MHz, DMSO-d6) δ 12.89 (s, 1H), 8.94 (s, 1H), 8.25 (s, 1H), 8.16 (s, 1H), 7.18 (s, 1H), 6.67 (s, 2H); 13C NMR (125 MHz, DMSO-d6) δ 160.7, 157.5, 145.4, 141.9, 137.2, 130.5, 117.7, 115.4; HRMS m/z 201.0753 (M+[C8H7N7]=201.0763).

Workup

  1. customAfter removal of volatiles
  2. filtrationfiltered hot
  3. customThe combined EtOAc extracts were evaporated to dryness
  4. dissolutionThe residue was dissolved in TFA/H2O (9:1, 60 mL)
  5. stirringthe solution was stirred at 0° C. for 4 h
  6. customVolatiles were evaporated in vacuo
  7. dissolutionthe residue was dissolved in 0.1 N NaOH/H2O//CH2Cl2 (100 mL/100 mL)
  8. extractionThe organic layer was extracted with 0.1 N NaOH/H2O (50 mL×2)
  9. washwashed [CH2Cl2 (2×50 mL)]
  10. customVolatiles were evaporated in vacuo
  11. washthe residue was washed (H2O, CH2Cl2)

Sources & evidence

ORD record
ord-7c54c253557f4106aae2cb08fc5b00b2
Source dataset
uspto-grants-2010_12
Patent number
US07855285B2

Reaction notes

Loading…