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

HRID 1641895Notes

Reaction equation

HRID 1641895 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 (which is prepared using the method described in international patent application WO 01/94368)(18.2 g, 40.9 mmol) is placed in an oven-dried flask under an atmosphere of argon. Dry CHCl3 (250 mL) and N,O-bis(trimethylsilyl)acetamide (50 mL) are added to the reaction mixture. The reaction mixture is refluxed for 1 hour. The reaction mixture is allowed to cool and the solvent is removed in vacuo. The resulting solid is taken up in MeOH (200 mL) and filtered the white solid is washed with MeOH (2×200 mL). The solid is suspended in water and sonicated for 30 minutes, filtered, washed with water (100 mL), MeOH (2×100 mL) and dried in vac oven to give the title compound. 1H NMR (DMSO, 400 MHz); 8.30 (m, 1H), 8.50 (m, 1H) 7.45-7.20 (m, 10H), 4.80-4.55 (m, 2H), 4.20 (m, 2H), 4.00 (m, 2H), 3.4 (s, 2H).

Workup

  1. customis placed in an oven-dried flask under an atmosphere of argon
  2. temperatureThe reaction mixture is refluxed for 1 hour
  3. temperatureto cool
  4. customthe solvent is removed in vacuo
  5. filtrationfiltered the white solid
  6. washis washed with MeOH (2×200 mL)
  7. customsonicated for 30 minutes
  8. filtrationfiltered
  9. washwashed with water (100 mL), MeOH (2×100 mL)
  10. customdried in vac oven

Sources & evidence

ORD record
ord-8cc3f313b37f43f6bcad11e195e48e27
Source dataset
uspto-grants-2012_02
Patent number
US08114877B2

Reaction notes

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