benzyl 4-{2-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propyl}piperazine-1-carboxylate → 4-[1-(1-methyl-2-piperazin-1-ylethyl)-1H-pyrazol-4-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine

HRID 1772779Notes

Reaction equation

HRID 1772779 reaction equation
[CH3:1][Si:2]([CH3:41])([CH3:40])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:11]2[N:12]=[CH:13][N:14]=[C:15]([C:16]3[CH:17]=[N:18][N:19]([CH:21]([CH3:39])[CH2:22][N:23]4[CH2:28][CH2:27][N:26](C(OCC5C=CC=CC=5)=O)[CH2:25][CH2:24]4)[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1.[H][H]>CO.[Pd]>[CH3:39][CH:21]([N:19]1[CH:20]=[C:16]([C:15]2[C:10]3[CH:9]=[CH:8][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:41])[CH3:40])[C:11]=3[N:12]=[CH:13][N:14]=2)[CH:17]=[N:18]1)[CH2:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 67054882benzyl 4-{2-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propyl}piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 670549204-[1-(1-methyl-2-piperazin-1-ylethyl)-1H-pyrazol-4-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidineYield 87.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 4-{2-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propyl}piperazine-1-carboxylate (0.30 g, 0.52 mmol; peak 1 from chiral separation) in methanol (10 mL) was hydrogenated in the presence of 10% palladium on carbon (10:90, Palladium:carbon black, 0.2 g, 0.2 mmol) under balloon pressure of hydrogen for 2 h. After filtering off catalyst, the filtrate was concentrated to give the desired product (0.20 g). LCMS calculated for C22H36N7OSi(M+H)+: m/z=442.3; Found: 442.4.

Workup

  1. filtrationAfter filtering off catalyst
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-805a70e3dd564799ab7370311d617c51
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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