Ammonium Hydroxide → (4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-nitro-phenyl)methanone

HRID 916755Notes

Reaction equation

HRID 916755 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)=[O:12])=[CH:9][N:8]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH4+:27].[OH-]>O1CCOCC1>[NH2:27][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)=[O:12])=[CH:9][N:8]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86760547(4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-nitro-phenyl)-methanone

Product 1

HCID 11859043(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-nitro-phenyl)methanoneYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-nitro-phenyl)-methanone (11.3 g, 30.5 mmol) and NH4OH (200 mL) in 1,4-Dioxane (300 mL) was heated to 50° C. in a pressure reactor. After 2 h the reaction was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 and washed with water. The organic layer was dried over MgSO4 and concentrated to afford the title compound as a yellow solid (10.37 g, 97%). MS: 352.1 (MH+); HPLC Rf: 5.56 min. (HPLC method 4).

Workup

  1. concentrationAfter 2 h the reaction was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b5dcfc661f294f41b429265b18fd6b41
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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