Dimethyl Sulfoxide → 4-[6-(4-Benzyloxyphenyl)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-2-chlorophenylamine

HRID 1433416Notes

Reaction equation

HRID 1433416 reaction equation
CS(C)=O.[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:22]3[N:23]=[CH:24][N:25]=[C:26](Cl)[C:21]=3[CH:20]=2)=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H-].[Na+].[NH2:39][C:40]1[CH:45]=[CH:44][C:43]([OH:46])=[CH:42][C:41]=1[Cl:47]>O>[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:35])([CH3:36])[CH3:34])[C:22]3[N:23]=[CH:24][N:25]=[C:26]([O:46][C:43]4[CH:44]=[CH:45][C:40]([NH2:39])=[C:41]([Cl:47])[CH:42]=4)[C:21]=3[CH:20]=2)=[CH:17][CH:18]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 871844-Amino-3-chlorophenolHCID 589310656-(4-benzyloxyphenyl)-4-chloro-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 589312304-[6-(4-Benzyloxyphenyl)-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy]-2-chlorophenylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After adding 12 ml of dimethylsulfoxide to the 6-(4-benzyloxyphenyl)-4-chloro-7-(2-trimethylsilanylethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine synthesized in Production Example 153-4, 141 mg (1.5 equivalents) of sodium hydride (60% dispersion, Aldrich) and 507 mg (1.5 equivalents) of 4-amino-3-chlorophenol were added while stirring, and stirring was then continued at room temperature for 10 minutes and then at 135-140° C. for 4 hours. The mixture was returned to room temperature, water was added, and liquid separation and extraction were performed with an ethyl acetate:tetrahydrofuran (5:1) mixed solvent. The organic layer was dried over sodium sulfate, concentrated and subjected to NH silica gel column chromatography (hexane-ethyl acetate) to obtain 1.20 g of the title compound.

Workup

  1. additionwere added
  2. stirringstirring
  3. waitat 135-140° C. for 4 hours
  4. customwas returned to room temperature
  5. customliquid separation and extraction
  6. additionmixed solvent
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9ff37a0d4ef4450f867b054911b414c9
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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