Methylamine → Ammonia

HRID 897130Notes

Reaction equation

HRID 897130 reaction equation
C([O:9][C@@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([N:24]2[CH:32]=[N:31][C:30]3[C:25]2=[N:26][C:27]([C:48]#[N:49])=[N:28][C:29]=3[NH:33][CH2:34][CH:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:12][C@@H:11]1[C:50]([NH:52][CH2:53][CH3:54])=[O:51])(=O)C1C=CC=CC=1.[CH3:55]N>[Pd].C(O)C>[NH3:24].[C:36]1([CH:35]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:34][NH:33][C:29]2[N:28]=[C:27]([CH2:48][NH:49][CH3:55])[N:26]=[C:25]3[C:30]=2[N:31]=[CH:32][N:24]3[C@@H:13]2[O:12][C@H:11]([C:50]([NH:52][CH2:53][CH3:54])=[O:51])[C@@H:10]([OH:9])[C@H:14]2[OH:15])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 2

HCID 6329MethylamineHCID 69431871HCID 69431871, compound

Product 2

HCID 222AmmoniaHCID 60018590HCID 60018590, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (0.2 g) was added to a solution of (2S,3R,4R,5R)-4-(benzoyloxy)-5-{2-cyano-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl}-2-[(ethylamino)carbonyl]tetrahydro-3-furanyl benzoate (1.0 g, 1.4 mmol) (Preparation 7) in 33% w/w methylamine in ethanol (75 ml). The reaction mixture was stirred under an atmosphere of hydrogen gas (4414 kPa, 60 psi) for 16 hours at room temperature. The solid was filtered off and the solvent was removed from the filtrate under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) increasing in polarity to dichloromethane:methanol:0.88 concentrated aqueous ammonia (90:10:1 by volume) to give the title compound (0.52 g) as a solid.

Workup

  1. filtrationThe solid was filtered off
  2. customthe solvent was removed from the filtrate under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane
  4. temperaturemethanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume) increasing in polarity to dichloromethane

Sources & evidence

ORD record
ord-9eb2633f9630451eacc8984c7b28f5c2
Source dataset
uspto-grants-2005_07
Patent number
US06921753B2

Reaction notes

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