Potassium Carbonate → 4-Chloro-5-((5-fluoro-2-methoxyphenyl)thio)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1052538Notes

Reaction equation

HRID 1052538 reaction equation
[Cl:1][C:2]1[C:3]2[C:10](I)=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:4]=2[N:5]=[CH:6][N:7]=1.[F:20][C:21]1[CH:22]=[CH:23][C:24]([O:28][CH3:29])=[C:25]([SH:27])[CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]I>[Cl:1][C:2]1[C:3]2[C:10]([S:27][C:25]3[CH:26]=[C:21]([F:20])[CH:22]=[CH:23][C:24]=3[O:28][CH3:29])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27590085-Fluoro-2-methoxythiophenolHCID 867069334-chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 901034234-Chloro-5-((5-fluoro-2-methoxyphenyl)thio)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidineYield 26%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
50 °C

Procedure

4-Chloro-5-iodo-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (200 mg, 0.49 mmol), 5-fluoro-2-methoxybenzenethiol (96 μl, 0.73 mmol), copper(I) iodide (139 mg, 0.73 mmol), potassium carbonate (135 mg, 0.98 mmol) and 2 ml dimethylformamide as solvent according to Preparation 86 but heating the reaction mixture at 50° C. overnight. The residue was purified using SP1® Purification System (0% to 15%, hexane-ethyl acetate) to give 56 mg (26% yield) of the title compound.

Workup

  1. customThe residue was purified
  2. customSP1® Purification System (0% to 15%, hexane-ethyl acetate)

Sources & evidence

ORD record
ord-4c00ed53850341eb81c02599a6bcf6e7
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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