Sodium Hydroxide → 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(2,2-diphenylethylamino)-N-(2-piperidin-1-ylethyl)purine-2-carboxamide

HRID 2184260Notes

Reaction equation

HRID 2184260 reaction equation
[C:1]1([CH:7]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:8][NH:9][C:10]2[N:18]=[C:17]([C:19]([NH:21][CH2:22][CH2:23][N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:20])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][N:14]3[C@@H:30]2[O:42][C@H:41]([CH2:43][O:44]C(=O)C)[C@@H:36]([O:37]C(=O)C)[C@H:31]2[O:32]C(=O)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>COCCOC>[OH:32][C@@H:31]1[C@H:36]([OH:37])[C@@H:41]([CH2:43][OH:44])[O:42][C@H:30]1[N:14]1[CH:13]=[N:12][C:11]2[C:15]1=[N:16][C:17]([C:19]([NH:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:20])=[N:18][C:10]=2[NH:9][CH2:8][CH:7]([C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 60004402HCID 60004402, compound

Product 1

HCID 98088349-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(2,2-diphenylethylamino)-N-(2-piperidin-1-ylethyl)purine-2-carboxamideYield 79.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
52.5 °C

Procedure

To a stirred solution of 6-[(2,2-diphenylethyl)amino]-N-[2-(1-piperidinyl)ethyl]-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-2-carboxamide (assumed to be 310 g, 0.426 moles) (Preparation 24) and 1,2-dimethoxyethane (1600 ml) was added 5M aqueous sodium hydroxide solution (640 ml, 3.2 moles) over a 45 minute period with cooling in ice. The resultant mixture was stirred at ambient temperature for 3 hours, and then the layers were separated. The stirred organic phase was then diluted with deionised water (1800 ml) with cooling. When the addition was complete, the resultant mixture was heated to 50-55° C. whereupon crystallisation started. To this heated and stirred suspension was added further deionised water (1800 ml) over a period of 50 minutes. Once the addition was complete, the resultant slurry was cooled to 10° C. over a period of 45 minutes and the resulting solid was then collected by filtration. The solid was washed with a solution of 1,2-dimethoxyethane (400 ml) and deionised water (800 ml) and was then dried at 55° C. under reduced pressure to give the crude title compound as a brown solid (203 g).

Workup

  1. temperaturewith cooling in ice
  2. customthe layers were separated
  3. additionThe stirred organic phase was then diluted with deionised water (1800 ml)
  4. temperaturewith cooling
  5. additionWhen the addition
  6. temperatureTo this heated
  7. additionwas added further deionised water (1800 ml) over a period of 50 minutes
  8. additionOnce the addition
  9. temperaturethe resultant slurry was cooled to 10° C. over a period of 45 minutes
  10. filtrationthe resulting solid was then collected by filtration
  11. washThe solid was washed with a solution of 1,2-dimethoxyethane (400 ml) and deionised water (800 ml)
  12. customwas then dried at 55° C. under reduced pressure

Sources & evidence

ORD record
ord-a6674b47a975479a975ed6fb51e1c044
Source dataset
uspto-grants-2005_05
Patent number
US06900309B1

Reaction notes

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