Saccharin → 4-(Dimethylamino)butyl 2-(4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetate disaccharin salt

HRID 445058Notes

Reaction equation

HRID 445058 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])=[O:18])=[CH:12][CH:11]=2)=[C:4]([NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[N:3]=1.[S:33]1([C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:37](=[O:38])[NH:36]1)(=[O:35])=[O:34]>C(#N)C>[S:33]1([C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:37](=[O:38])[NH:36]1)(=[O:34])=[O:35].[S:33]1([C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:37](=[O:38])[NH:36]1)(=[O:34])=[O:35].[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]([CH3:25])[CH3:26])=[O:18])=[CH:14][CH:15]=2)=[C:4]([NH:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[N:3]=1

Participants

4

Reactant 2

HCID 5143Saccharin3×HCID 497799954-(Dimethylamino)butyl 2-[4-[[2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]methyl]phenyl]acetate2×

Product 1

HCID 497799944-(Dimethylamino)butyl 2-(4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetate disaccharin salt

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

The solution of the product from step (vii) was diluted with acetonitrile (9.3 g) and activated carbon (0.2 g) was added. The mixture was stirred at 25° C. for 30 minutes, filtered through a paper filter (1 μm mesh), and washed with acetonitrile (7.0 g). Saccharin (1.32 g, 7.21 mmol) was added to the filtrate and then the quantity of the product from step is (vii) in the solution was determined by HPLC analysis. The equivalent of saccharin for the product from step (vii) was adjusted to 2.00 molar ratio with an additional charge of saccharin (0.34 g, 1.86 mmol) and the solution was concentrated under reduced pressure. The corresponding residue was diluted with acetonitrile (4.1 g) and ethyl acetate (9.6 g), heated to 40° C. and seeded with form A crystals of the title compound. After the mixture was stirred at 40° C. for 1 hour, ethyl acetate (10.6 g) was added. The mixture was stirred at 40° C. for 1 hour, cooled to 10° C. and stirred for 2 hours. The resulting solid was collected by filtration, washed with combined solution of acetonitrile (0.8 g) and ethyl acetate (3.0 g), and dried under reduced pressure to give a crude sample of the subtitle compound as a white solid, 3.11 g.

Workup

  1. additionwas added
  2. filtrationfiltered through a paper
  3. filtrationfilter (1 μm mesh)
  4. washwashed with acetonitrile (7.0 g)
  5. concentrationthe solution was concentrated under reduced pressure
  6. additionThe corresponding residue was diluted with acetonitrile (4.1 g) and ethyl acetate (9.6 g)
  7. temperatureheated to 40° C.
  8. stirringAfter the mixture was stirred at 40° C. for 1 hour
  9. additionethyl acetate (10.6 g) was added
  10. stirringThe mixture was stirred at 40° C. for 1 hour
  11. temperaturecooled to 10° C.
  12. stirringstirred for 2 hours
  13. filtrationThe resulting solid was collected by filtration
  14. washwashed with combined solution of acetonitrile (0.8 g) and ethyl acetate (3.0 g)
  15. customdried under reduced pressure

Sources & evidence

ORD record
ord-eb456d449e9f45258d6619580638ec3f
Source dataset
uspto-grants-2013_07
Patent number
US08476288B2

Reaction notes

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