Potassium Carbonate → HCID 90103343, compound

HRID 1052421Notes

Reaction equation

HRID 1052421 reaction equation
Br[C:2]1[C:10]2[C:9]([Cl:11])=[N:8][CH:7]=[N:6][C:5]=2[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([SH:28])[CH:25]=[CH:26][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]I>[Cl:11][C:9]1[C:10]2[C:2]([S:28][C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([O:21][CH3:20])[CH:23]=3)=[CH:3][N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]=2[N:6]=[CH:7][N:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 849893-MethoxybenzenethiolHCID 583960415-bromo-4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 90103343HCID 90103343, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

5-Bromo-4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (300 mg, 0.74 mmol) was dissolved in 3 mL dimethylformamide. 3-Methoxybenzenethiol (140 mg, 1.10 mmol), copper(I) iodide (205 mg, 1.1 mmol) and potassium carbonate (152 mg, 1.1 mmol) were added. The reaction vessel was sealed and submitted to three vacuum-nitrogen cycles. The reaction was heated at 70° C. for 5 h. The mixture was poured into water-ice and extracted twice with ethyl acetate. The organics were dried over sodium sulphate, filtered and concentrated under reduced pressure. The crude was purified using SP1® Purification System (0% to 20%, hexane-ethyl acetate) to obtain 128 mg (70% yield) of the title compound as a solid. Purity 83%.

Workup

  1. customThe reaction vessel was sealed
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe organics were dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude was purified
  7. customSP1® Purification System (0% to 20%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-557f1c2ccc7344528bf1e41d19a184dc
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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