Dimethylamine → Ammonia

HRID 1295642Notes

Reaction equation

HRID 1295642 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[NH:26][C:12]3[N:13]=[CH:14][N:15]=[C:16]([NH:17][C@@H:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH3:19])[C:11]=3[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[CH3:27][NH:28][CH3:29]>C(O)C>[NH3:13].[CH3:27][N:28]([CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[NH:26][C:12]3[N:13]=[CH:14][N:15]=[C:16]([NH:17][C@@H:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH3:19])[C:11]=3[CH:10]=2)[CH:6]=[CH:7][CH:8]=1)[CH3:29]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 69183175HCID 69183175, compound

Product 2

HCID 222AmmoniaYield 1%HCID 10156073HCID 10156073, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 240 mg (0.5 mmol) crude [6-(3-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-((R)-1-phenyl-ethyl)-amine in 15 ml 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 clear solution is cooled and the solvent evaporated. The residue is purified with flash chromatography using dichloromethane/ethanol 95:5 and then dichloromethane/ethanol 9:1 plus 1% conc. ammonia to give the title compound; m.p. 108-110° C.; MS-ES+: (M+H)+=372.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 h
  3. temperatureThe clear solution is cooled
  4. customthe solvent evaporated
  5. customThe residue is purified with flash chromatography

Sources & evidence

ORD record
ord-ff34fb0a02c544779b289187db58eb6a
Source dataset
uspto-grants-2007_07
Patent number
US07244729B2

Reaction notes

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