Cesium carbonate → HCID 86706962, compound

HRID 1750291Notes

Reaction equation

HRID 1750291 reaction equation
I[C:2]1[C:10]2[C:9]([N:11]([CH3:13])[CH3:12])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:3]=1.[OH:22][CH2:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.[Cl-].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][N:11]([CH3:13])[C:9]1[C:10]2[C:2]([C:28]3[CH:29]=[C:24]([CH2:23][OH:22])[CH:25]=[CH:26][CH:27]=3)=[CH:3][N:4]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:5]=2[N:6]=[CH:7][N:8]=1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 86706942HCID 86706942, compound

Product 1

HCID 86706962HCID 86706962, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 5234Sodium ChlorideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 5-iodo-N,N-dimethyl-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-amine (C3) (418 mg, 1.00 mmol), [3-(hydroxymethyl)phenyl]boronic acid (228 mg, 1.50 mmol), tetrakis(triphenylphosphine)palladium(0) (115 mg, 0.100 mmol), and cesium carbonate (625 mg, 1.92 mmol) in 1,4-dioxane (6 mL) and water (1.5 mL) was purged with nitrogen, then heated under microwave irradiation at 120° C. for 20 minutes. The reaction mixture was diluted with saturated aqueous sodium chloride solution (50 mL) and extracted with dichloromethane (3×60 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatography on silica gel (Gradient: 2% to 17% ethyl acetate in petroleum ether) afforded the product as a brown oil. Yield: 369 mg, 0.926 mmol, 93%. LCMS m/z 399.0 [M+H+].

Workup

  1. extractionextracted with dichloromethane (3×60 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-44cbbfd262154380870271f56b03ac73
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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