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

HRID 1819327Notes

Reaction equation

HRID 1819327 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[Cl:9][C:10]1[CH:44]=[CH:43][CH:42]=[CH:41][C:11]=1[CH2:12][N:13]1[C:21]2[C:20](=[O:22])[N:19]([CH3:23])[C:18](=[O:24])[N:17]([CH3:25])[C:16]=2[C:15]([OH:26])=[C:14]1[N:27]1[CH2:32][CH2:31][CH2:30][C@@H:29]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:28]1.S([O-])(O)(=O)=O.[K+]>CN(C)C=O>[Cl:9][C:10]1[CH:44]=[CH:43][CH:42]=[CH:41][C:11]=1[CH2:12][N:13]1[C:21]2[C:20](=[O:22])[N:19]([CH3:23])[C:18](=[O:24])[N:17]([CH3:25])[C:16]=2[C:15]([O:26][CH3:1])=[C:14]1[N:27]1[CH2:32][CH2:31][CH2:30][C@@H:29]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:39])[CH3:37])[CH2:28]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 516920Potassium bisulfateHCID 57886892tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-7-hydroxy-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 57886947tert-Butyl {(3R)-1-[5-(2-chlorobenzyl)-7-methoxy-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamateYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (41 mg) and methyl iodide (13 μl) were added to a solution of tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-7-hydroxy-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (50 mg) in N,N-dimethylformamide (2 ml), and the resulting mixture was stirred at room temperature for 5 hours. A 10% aqueous potassium hydrogensulfate solution was added to the reaction solution, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with a 10% aqueous potassium hydrogensulfate solution and a saturated aqueous sodium chloride solution, dried over sodium sulfate and then filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a preparative thin-layer chromatography (hexane/ethyl acetate=1/1) to obtain the title compound (17 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate (100 ml)
  2. washThe organic layer was washed with a 10% aqueous potassium hydrogensulfate solution
  3. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by a preparative thin-layer chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-0ed11b7538774ee2a07f433e8654fa8e
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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