Water → 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

HRID 1819298Notes

Reaction equation

HRID 1819298 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]([OH:24])=[N:17][C:16]=2[C:15]([C:25]#[N: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.O>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]([CH3:1])[C:16]=2[C:15]([C:25]#[N: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]([CH3:38])([CH3:39])[CH3:37])[CH2:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178481598HCID 178481598, compound

Product 1

HCID 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}carbamateYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Potassium carbonate (700 mg) and methyl iodide (0.34 ml) were added to a solution of tert-butyl {(3R)-1-[5-(2-chlorobenzyl)-7-cyano-2-hydroxy-3-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (1.3 g) in N,N-dimethylformamide, and the resulting mixture was stirred at 25° C. for 4 hours. After the reaction, water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water 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 silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain the title compound (1.1 g) as a white solid.

Workup

  1. additionwas added to the reaction solution
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by a silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-b37a77c57ac7469c9389d7e4d1b3c616
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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