Chlorotrimethylsilane → N-(4-(5-cyano-4-(cyclopropylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamide

HRID 2281496Notes

Reaction equation

HRID 2281496 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:23][CH:24]2[CH2:26][CH2:25]2)[C:5]2[C:10]([C:11]#[N:12])=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]=2[N:7]=1.[NH2:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]([CH3:38])[C:35](=[O:37])[CH3:36])=[CH:30][CH:29]=1.C[Si](Cl)(C)C>C(O)CCC>[C:11]([C:10]1[C:5]2[C:4]([NH:23][CH:24]3[CH2:25][CH2:26]3)=[N:3][C:2]([NH:27][C:28]3[CH:29]=[CH:30][C:31]([N:34]([CH3:38])[C:35](=[O:37])[CH3:36])=[CH:32][CH:33]=3)=[N:7][C:6]=2[NH:8][CH:9]=1)#[N:12]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 67068N-(4-Aminophenyl)-N-methylacetamideHCID 579903512-chloro-4-(cyclopropylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Product 1

HCID 57990402N-(4-(5-cyano-4-(cyclopropylamino)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)-N-methylacetamideYield 32.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-chloro-4-(cyclopropylamino)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (165 mg, 0.425 mmol), N-(4-aminophenyl)-N-methylacetamide (107 mg, 0.652 mmol) and trimethylsilyl chloride (0.200 mL, 1.58 mmol) in nBuOH (4 mL) was stirred at 135° C. for 20 h. It was concentrated in vacuo. The residue was purified by HPLC to give the titled compound (50 mg). MS 362.3 (M+H); UV 202.8, 254.0, 280.4 nm.

Workup

  1. concentrationIt was concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-a1352ee4eae54bbaa44696f59845cc9a
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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