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

HRID 1819313Notes

Reaction equation

HRID 1819313 reaction equation
[Xe][F:2].[Cl:3][C:4]1[CH:37]=[CH:36][CH:35]=[CH:34][C:5]=1[CH2:6][N:7]1[C:15]2[C:14](=[O:16])[N:13]([CH3:17])[C:12](=[O:18])[N:11]([CH3:19])[C:10]=2[CH:9]=[C:8]1[N:20]1[CH2:25][CH2:24][CH2:23][C@@H:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:21]1.C(=O)([O-])O.[Na+]>C(#N)C>[Cl:3][C:4]1[CH:37]=[CH:36][CH:35]=[CH:34][C:5]=1[CH2:6][N:7]1[C:15]2[C:14](=[O:16])[N:13]([CH3:17])[C:12](=[O:18])[N:11]([CH3:19])[C:10]=2[C:9]([F:2])=[C:8]1[N:20]1[CH2:25][CH2:24][CH2:23][C@@H:22]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:32])[CH3:30])[CH2:21]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 57886903tert-Butyl {(3R)-1-[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}carbamateHCID 136857710Fluoroxenon

Product 1

HCID 57887006tert-Butyl {(3R)-1-[5-(2-chlorobenzyl)-7-fluoro-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamateYield 4.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Xenon fluoride (56 mg) was added to a solution of tert-butyl {(3R)-1-[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 (1.00 g) in acetonitrile (10 ml), and the resulting mixture was stirred overnight at room temperature. After a saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, the acetonitrile was distilled off under reduced pressure, and the residue was extracted twice with chloroform (50 ml). The organic layer was dried over sodium sulfate and filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a thin-layer silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain the title compound (8 mg).

Workup

  1. distillationthe acetonitrile was distilled off under reduced pressure
  2. extractionthe residue was extracted twice with chloroform (50 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by a thin-layer silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-9fcd64fdc0bd42e490cb764f4502043a
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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