3-Hydroxycyclobutane-1-carbonitrile → 3-((2-Chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)cyclobutanecarbonitrile

HRID 1487674Notes

Reaction equation

HRID 1487674 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([I:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[N:7]=1.[OH:21][CH:22]1[CH2:25][CH:24]([C:26]#[N:27])[CH2:23]1.CC([O-])(C)C.[Na+]>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([O:21][CH:22]2[CH2:25][CH:24]([C:26]#[N:27])[CH2:23]2)[C:5]2[C:10]([I:11])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 224086853-Hydroxycyclobutane-1-carbonitrileHCID 23676156Sodium t-butoxideHCID 866796212,4-dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo(2,3-d)pyrimidine

Product 1

HCID 867265013-((2-Chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)cyclobutanecarbonitrileYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

2,4-Dichloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (1 equiv), 3-hydroxycyclobutanecarbonitrile (1.1 equiv), sodium 2-methylpropan-2-olate (1.2 equiv) and 1,4-dioxane (0.14 M) were combined in a sealable vessel with a stir bar. The resulting mixture was put under nitrogen atmosphere, sealed, stirred vigorously, and heated at 70° C. for 16 h. After cooling to room temperature, the reaction mixture was purified using silica gel chromatography (0 to 50% ethyl acetate in hexane) to give the title compound (77% yield). MS (ESI) m/z 505.0 [M+H]+.

Workup

  1. customsealed
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-baa47b9c7e704a72b5b42b9144eefb35
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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