Dimethylamine → Ammonia

HRID 133019Notes

Reaction equation

HRID 133019 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25]Cl)=[CH:21][CH:20]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:27][NH:28][CH3:29]>C(O)C>[NH3:9].[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25][N:28]([CH3:29])[CH3:27])=[CH:21][CH:20]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 11383626(3-Chloro-4-fluoro-phenyl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

Product 2

HCID 222AmmoniaYield 1%HCID 10157552(3-Chloro-4-fluoro-phenyl)-[6-(4-dimethylaminomethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 200 mg (0.5 mmol) crude (3-chloro-4-fluoro-phenyl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine in 15 ml absolute ethanol is treated with 0.8 ml (5 mmol) of a 33% solution of dimethylamine in ethanol (Fluka, Buchs, Switzerland) and then heated under reflux for 1 h. The almost clear solution is cooled and the solvent evaporated. The residue is dissolved in a mixture of dichloromethane and ethanol (95:5), washed with water, dried over sodium sulfate and the solvent evaporated. Purification of the crude material through flash chromatography using first dichloromethane/ethanol 95:5 plus 1% conc. ammonia and then dichloromethane/ethanol 9:1 plus 1% conc. ammonia gives the title compound; m.p. 274-276° C.; MS-ES+: (M+H)+=396.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 h
  3. temperatureThe almost clear solution is cooled
  4. customthe solvent evaporated
  5. dissolutionThe residue is dissolved in a mixture of dichloromethane and ethanol (95:5)
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customthe solvent evaporated
  9. customPurification of the crude material through flash chromatography

Sources & evidence

ORD record
ord-5ed3c4dd8ab0452cbd2cc291ed6d37ac
Source dataset
uspto-grants-2008_06
Patent number
US07390805B2

Reaction notes

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