Dimethyl Sulfoxide → tert-Butyl {(3R)-1-[7-(aminocarbonyl)-5-(2-chlorobenzyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate

HRID 1819305Notes

Reaction equation

HRID 1819305 reaction equation
CS(C)=O.[Cl:5][C:6]1[CH:41]=[CH:40][CH:39]=[CH:38][C:7]=1[CH2:8][N:9]1[C:17]2[C:16](=[O:18])[N:15]([CH3:19])[C:14](=[O:20])[N:13]([CH3:21])[C:12]=2[C:11]([C:22]#[N:23])=[C:10]1[N:24]1[CH2:29][CH2:28][CH2:27][C@@H:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:25]1.C(=O)([O-])[O-:43].[K+].[K+].OO>O>[NH2:23][C:22]([C:11]1[C:12]2[N:13]([CH3:21])[C:14](=[O:20])[N:15]([CH3:19])[C:16](=[O:18])[C:17]=2[N:9]([CH2:8][C:7]2[CH:38]=[CH:39][CH:40]=[CH:41][C:6]=2[Cl:5])[C:10]=1[N:24]1[CH2:29][CH2:28][CH2:27][C@@H:26]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH2:25]1)=[O:43]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 57886926tert-Butyl {(3R)-1-[5-(2-chlorobenzyl)-7-cyano-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate

Product 1

HCID 57886907tert-Butyl {(3R)-1-[7-(aminocarbonyl)-5-(2-chlorobenzyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamateYield 84.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

To a mixed solution of dimethyl sulfoxide (250 ml) and water (25 ml) were added tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-7-cyano-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (17.9 g) and potassium carbonate (4.7 g). In a water bath, an aqueous hydrogen peroxide solution (a 30-35% aqueous solution, 17 ml) was added dropwise and the resulting mixture was stirred at 25° C. for 15 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed three times with water and then once with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure to obtain the title compound (15.6 g) as a light-yellow amorphous substance.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed three times with water
  3. dry with materialonce with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-affac74e23f6408180c3190d4b127fb6
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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