Dimethylamine → HCID 10225808, compound

HRID 1295641Notes

Reaction equation

HRID 1295641 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:17]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([CH2:31]Cl)=[CH:27][CH:26]=4)[NH:22][C:18]=3[N:19]=[CH:20][N:21]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][NH:34][CH3:35]>C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:17]3[CH:24]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([CH2:31][N:34]([CH3:35])[CH3:33])=[CH:27][CH:26]=4)[NH:22][C:18]=3[N:19]=[CH:20][N:21]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 69179584HCID 69179584, compound

Product 1

HCID 10225808HCID 10225808, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 220 mg (0.5 mmol) crude (4-benzyloxy-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 resulting 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. The solid material is then suspended in ether stirred for 5 min and filtered. Purification of the crude material through flash chromatography using dichloromethane/ethanol 9:1 plus 1% conc. ammonia gives the title compound; m.p. 272-274° C.; MS-ES+: (M+H)+=450.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 h
  3. temperatureThe resulting 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. filtrationfiltered
  10. customPurification of the crude material through flash chromatography

Sources & evidence

ORD record
ord-0c8489407b314e03a1c0f70cd2c56806
Source dataset
uspto-grants-2007_07
Patent number
US07244729B2

Reaction notes

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