Chlorotrimethylsilane → N-(4-(piperazin-1-yl)phenyl)-4-(piperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

HRID 2281388Notes

Reaction equation

HRID 2281388 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:29][CH2:28][N:27]([C:30](=[O:32])[CH3:31])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C[Si](Cl)(C)C>CCCCO>[N:24]1([C:21]2[CH:20]=[CH:19][C:18]([NH:17][C:2]3[N:3]=[C:4]([N:11]4[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]4)[C:5]4[CH:10]=[CH:9][NH:8][C:6]=4[N:7]=3)=[CH:23][CH:22]=2)[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]1.[N:11]1([C:4]2[C:5]3[CH:10]=[CH:9][NH:8][C:6]=3[N:7]=[C:2]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([N:24]4[CH2:25][CH2:26][N:27]([C:30](=[O:32])[CH3:31])[CH2:28][CH2:29]4)=[CH:22][CH:23]=3)[N:3]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 7362691-[4-(4-Aminophenyl)piperazin-1-yl]ethan-1-oneHCID 579903122-chloro-4-(piperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine

Product 2

HCID 44467607N-(4-(piperazin-1-yl)phenyl)-4-(piperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-amineHCID 444676081-(4-(4-(4-(piperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A mixture of 2-chloro-4-(piperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine (123 mg, 0.520 mmol), 1-(4-(4-aminophenyl)piperazin-1-yl)ethanone (200 mg, 0.913 mmol) and trimethylsilyl chloride (0.200 mL, 1.58 mmol) in n-BuOH (5 mL) was stirred at 120° C. for 20 h. n-BuOH was removed in vacuo. The residue was purified by HPLC to give N-(4-(piperazin-1-yl)phenyl)-4-(piperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (5 mg) (MS 378.5 (M+H)) and 1-(4-(4-(4-(piperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (31 mg) (MS 420.5 (M+H); UV 205.8, 275.8 nm).

Workup

  1. customwas removed in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-595217a619d94106be1b224f9e79242c
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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