N,O-bis(trimethylsilyl)acetamide → HCID 178418823, compound

HRID 1882579Notes

Reaction equation

HRID 1882579 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][NH:12]2)=[C:8]([NH:15][CH2:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:7]=1)=[O:5].C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C>C(Cl)(Cl)Cl>[CH3:2][O:3][C:4]([C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][NH:12]2)=[C:8]([NH:15][CH2:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 178499113HCID 178499113, compound

Product 1

HCID 178418823HCID 178418823, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6-(2,2-Diphenyl-ethylamino)-9H-purine-2-carboxylic acid methyl ester hydrochloride (prepared using the procedure described in international patent application WO 2001/94368) (35 g, 85.3 mmol) is placed in a flask under an atmosphere of argon. Dry CHCl3 (300 ml) and N,O-bis(trimethylsilyl)acetamide (61 ml) are added and the reaction mixture is refluxed for 1 hour. The reaction mixture is allowed to cool and any volatiles removed in vacuo. To the resulting oil is added MeOH (300 ml). The resulting white solid is filtered and washed with MeOH (2×200 ml) and then dried in a vacuum oven to give the title compound. 1H NMR (DMSO, 400 MHz).

Workup

  1. customis placed in a flask under an atmosphere of argon
  2. temperaturethe reaction mixture is refluxed for 1 hour
  3. temperatureto cool
  4. customany volatiles removed in vacuo
  5. additionTo the resulting oil is added MeOH (300 ml)
  6. filtrationThe resulting white solid is filtered
  7. washwashed with MeOH (2×200 ml)
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-e3be02990458411588fc595fec9bd8b0
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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