Water → tert-Butyl {(3R)-1-[5-(2-chloro-5-fluorobenzyl)-2,7-dicyano-3-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate

HRID 1819325Notes

Reaction equation

HRID 1819325 reaction equation
[C-:1]#[N:2].[Na+].[Cl:4][C:5]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:6]=1[CH2:7][N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH3:18])[C:13](S(C)(=O)=O)=[N:12][C:11]=2[C:10]([C:23]#[N:24])=[C:9]1[N:25]1[CH2:30][CH2:29][CH2:28][C@@H:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:26]1.O>O1CCCC1>[Cl:4][C:5]1[CH:42]=[CH:41][C:40]([F:43])=[CH:39][C:6]=1[CH2:7][N:8]1[C:16]2[C:15](=[O:17])[N:14]([CH3:18])[C:13]([C:1]#[N:2])=[N:12][C:11]=2[C:10]([C:23]#[N:24])=[C:9]1[N:25]1[CH2:30][CH2:29][CH2:28][C@@H:27]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:26]1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 57886996tert-butyl {(3R)-1-[5-(2-chloro-5-fluorobenzyl)-7-cyano-3-methyl-2-(methylsulfonyl)-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate

Product 1

HCID 86625682tert-Butyl {(3R)-1-[5-(2-chloro-5-fluorobenzyl)-2,7-dicyano-3-methyl-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamateYield 93.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An aqueous solution (2 ml) of sodium cyanide (338 mg) was added to a solution of tert-butyl {(3R)-1-[5-(2-chloro-5-fluorobenzyl)-7-cyano-3-methyl-2-(methylsulfonyl)-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (890 mg) in tetrahydrofuran (10 ml), and the resulting mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate (200 ml). The organic layer was washed with a 10% aqueous potassium carbonate 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 silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain the title compound (758 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate (200 ml)
  2. washThe organic layer was washed with a 10% aqueous potassium carbonate 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 silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-698e3984a0754f97abfa8df923855e80
Source dataset
uspto-grants-2009_10
Patent number
US07601728B2

Reaction notes

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