Hydrochloric Acid → 4-[1-(1-methyl-2-oxo-2-piperazin-1-ylethyl)-1H-pyrazol-4-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine

HRID 1772787Notes

Reaction equation

HRID 1772787 reaction equation
[CH3:1][Si:2]([CH3:39])([CH3:38])[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]([CH3:37])[C:22]([N:24]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)=[O:23])[CH:20]=3)[C:10]=2[CH:9]=[CH:8]1.Cl.O1CCOCC1>C(Cl)Cl>[CH3:37][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])([CH3:39])[CH3:38])[C:11]=3[N:12]=[CH:13][N:14]=2)[CH:17]=[N:18]1)[C:22](=[O:23])[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67054951tert-butyl 4-{2-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanoyl}piperazine-1-carboxylate

Product 1

HCID 670549604-[1-(1-methyl-2-oxo-2-piperazin-1-ylethyl)-1H-pyrazol-4-yl]-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidineYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 4-{2-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanoyl}piperazine-1-carboxylate (3.14 g, 5.65 mmol) in methylene chloride (20 mL) was added 4.0 M of hydrogen chloride in 1,4-dioxane (7.06 mL, 28.2 mmol). The reaction mixture was stirred at RT for 1 h, then evaporated to dryness under reduced pressure. The residue was diluted with EtOAc and washed with 1 N NaOH, brine, dried over magnesium sulfate, and concentrated to dryness under reduced pressure to give the desired product (2.57 g, 99.8%). LCMS calculated for C22H34N7O2Si (M+H)+: m/z=456.3; Found: 456.2.

Workup

  1. customevaporated to dryness under reduced pressure
  2. additionThe residue was diluted with EtOAc
  3. washwashed with 1 N NaOH, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-5826e149c6474edca033f693f615564f
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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