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

HRID 916756Notes

Reaction equation

HRID 916756 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[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+].[Cl-].O>O1CCOCC1.CCO.[Fe]>[NH2:1][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=3)=[O:12])=[CH:9][N:8]([CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 11859043(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-nitro-phenyl)methanone

Product 1

HCID 11859044(4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-amino-phenyl)methanoneYield 100%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Fe (8.24 g, 147.55 mmol) was added to a solution of (4-Amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(3-nitro-phenyl)methanone (10.37 g, 29.51 mmol) and NH4Cl (6.31 g, 118.0 mmol) in 1,4-Dioxane (200 mL), EtOH (150 mL), and water (100 mL). The resulting suspension was heated to reflux for 2 h, at this time the reaction was cooled to room temperature then filtered through celite eluting with EtOAc. The filtrate was dried over MgSO4 and concentrated to afford the title compound as a yellow solid (9.48 g, 100%). MS: 322.3 (MH+); HPLC Rf: 4.55 min. (HPLC method 4).

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 2 h, at this time the reaction
  3. filtrationthen filtered through celite
  4. washeluting with EtOAc
  5. dry with materialThe filtrate was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b33c42288a4046c0ab1bc298ecc116fd
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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