Chlorotrimethylsilane → HCID 44467743, compound

HRID 2381616Notes

Reaction equation

HRID 2381616 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:5]2[CH:10]=[CH:9][NH:8][C:6]=2[N:7]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29](=[O:31])[CH3:30])[CH2:25][CH2:24]2)=[CH:19][CH:18]=1.C[Si](Cl)(C)C>CCCCO>[N:23]1([C:20]2[CH:19]=[CH:18][C:17]([NH:16][C:2]3[N:3]=[C:4]([N:11]4[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:22][CH:21]=2)[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]1.[N:11]1([C:4]2[C:5]3[CH:10]=[CH:9][NH:8][C:6]=3[N:7]=[C:2]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([N:23]4[CH2:24][CH2:25][N:26]([C:29](=[O:31])[CH3:30])[CH2:27][CH2:28]4)=[CH:21][CH:22]=3)[N:3]=2)[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 57990393HCID 57990393, compound

Product 2

HCID 44467743HCID 44467743, compoundHCID 44467744HCID 44467744, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A mixture of 2-chloro-4-(pyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine (116 mg, 0.521 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-(pyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (3 mg) (MS 364.5 (M+H)) and 1-(4-(4-(4-(pyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)phenyl)piperazin-1-yl)ethanone (30 mg) (MS 406.5 (M+H)).

Workup

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

Sources & evidence

ORD record
ord-b519c674756f4bf385af3365abb7bf06
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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