Trityl chloride → HCID 135461120, compound

HRID 2264873Notes

Reaction equation

HRID 2264873 reaction equation
[NH:1]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=[C:2]1[NH2:3].[C:12](Cl)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C[Si](N[Si](C)(C)C)(C)C>[C:12]([NH:3][C:2]1[NH:1][C:10](=[O:11])[C:9]2[N:8]=[CH:7][N:6]([C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:5]=2[N:4]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 135398634Guanine

Product 1

HCID 135461120HCID 135461120, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 13838HexamethyldisilazaneSolvent

Procedure

Freshly activated guanine (0.45 g, 3 mmol) and (NH4)2SO4 (60 mg) were stirred in HMDS (50 mL) under reflux for 24 h to give a clear solution. Volatiles were evaporated in vacuo, and the residue was dissolved in dried CH3CN (50 mL). Trityl chloride (3.5 g, 12.6 mmol) was added, and the solution was stirred under reflux for 48 h. Volatiles were evaporated in vacuo, and the residue was dissolved in CH2Cl2 (10 mL). NH3/H2O (28-30%, 30 mL) was added, and precipitation was observed immediately. The mixture was stirred at ambient temperature overnight. Volatiles were evaporated in vacuo, and the residue was washed (H2O, CH2Cl2) to give 2-N,9-bistritylguanine as a solid (1.37 g, 72%), which was further purified by dissolving in MeOH/CH2Cl2 (1:15) and filtering: 1H NMR (500 MHz, DMSO-d6) δ 10.75 (s, 1H), 7.35 (s, 1H), 7.08-7.19 (m, 19H), 6.87 (d, J=7.4 Hz, 6H), 6.81 (d, J=7.3 Hz, 6H); 13C NMR (125 MHz, DMSO-d6) δ 157.3, 151.8, 151.0, 145.3, 142.4, 139.6, 129.6, 128.8, 128.5, 128.3, 127.6, 126.9, 120.3, 75.4, 71.1; HRMS m/z 635.2675 (M+[C43H33N5O]=635.2685).

Workup

  1. temperatureunder reflux for 24 h
  2. customto give a clear solution
  3. customVolatiles were evaporated in vacuo
  4. dissolutionthe residue was dissolved in dried CH3CN (50 mL)
  5. temperatureunder reflux for 48 h
  6. customVolatiles were evaporated in vacuo
  7. dissolutionthe residue was dissolved in CH2Cl2 (10 mL)
  8. additionNH3/H2O (28-30%, 30 mL) was added
  9. customprecipitation
  10. stirringThe mixture was stirred at ambient temperature overnight
  11. customVolatiles were evaporated in vacuo
  12. washthe residue was washed (H2O, CH2Cl2)

Sources & evidence

ORD record
ord-e43e0be4836f44cdad7bf909dcb39383
Source dataset
uspto-grants-2010_12
Patent number
US07855285B2

Reaction notes

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