Ammonium Hydroxide → (4-Amino-7-cyclopentyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-(4'-dimethylamino-biphenyl-3-yl)-methanone

HRID 916771Notes

Reaction equation

HRID 916771 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:14]=[C:15]([C:19]4[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=4)[CH:16]=[CH:17][CH:18]=3)=[O:12])=[CH:9][N:8]([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[NH4+:33].[OH-]>O1CCOCC1>[NH2:33][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:14]=[C:15]([C:19]4[CH:24]=[CH:23][C:22]([N:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=4)[CH:16]=[CH:17][CH:18]=3)=[O:12])=[CH:9][N:8]([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86760550(4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(4'-dimethylamino-biphenyl-3-yl)methanone

Product 1

HCID 67219507(4-Amino-7-cyclopentyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-(4'-dimethylamino-biphenyl-3-yl)-methanoneYield 74%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (4-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-(4′-dimethylamino-biphenyl-3-yl)-methanone ((40 mg, 0.089 mmol) and NH4OH (2 mL) in 1,4-dioxane (2 mL) was heated to 50° C. in a sealed tube. After 12 h the reaction was concentrated under reduced pressure and purified by flash column chromatography (CH2Cl2/MeOH 95:5) to afford the title compound as a yellow solid (28 mg, 74%). MS: 426.0 (MH+); HPLC Rf: 7.38 min. (HPLC method 4).

Workup

  1. concentrationAfter 12 h the reaction was concentrated under reduced pressure
  2. custompurified by flash column chromatography (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-7b8020825369418eb9fa1e015b08dde9
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Reaction notes

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