Tetrabutylammonium Fluoride → 4-(2-fluoro-4-{[1-(4-fluoro-phenylcarbamoyl)-cyclopropanecarbonyl]-amino}-phenoxy)-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid

HRID 1011301Notes

Reaction equation

HRID 1011301 reaction equation
C([O:3][C:4]([C:6]1[N:38]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:9]2[N:10]=[CH:11][N:12]=[C:13]([O:14][C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]4([C:27](=[O:36])[NH:28][C:29]5[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=5)[CH2:26][CH2:25]4)=[O:23])=[CH:17][C:16]=3[F:37])[C:8]=2[CH:7]=1)=[O:5])C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)(=O)C>[F:37][C:16]1[CH:17]=[C:18]([NH:21][C:22]([C:24]2([C:27](=[O:36])[NH:28][C:29]3[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=3)[CH2:25][CH2:26]2)=[O:23])[CH:19]=[CH:20][C:15]=1[O:14][C:13]1[C:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[N:38]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[C:9]=2[N:10]=[CH:11][N:12]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 589380244-(2-fluoro-4-{[1-(4-fluoro-phenylcarbamoyl)-cyclopropanecarbonyl]-amino}-phenoxy)-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Product 1

HCID 589380284-(2-fluoro-4-{[1-(4-fluoro-phenylcarbamoyl)-cyclopropanecarbonyl]-amino}-phenoxy)-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acidYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask equipped with a magnetic stir bar was added 4-(2-fluoro-4-{[1-(4-fluoro-phenylcarbamoyl)-cyclopropanecarbonyl]-amino}-phenoxy)-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.069 g, 0.10 mmol, 1.0 eq.), and a 1M tetrabutylammonium fluoride solution (5 ml). The reaction was allowed to stir at overnight. The reaction was diluted with ethyl acetate, washed with (2×) H2O (50 ml), 1M HCl (2×), sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo, affording 4-(2-fluoro-4-{[1-(4-fluoro-phenylcarbamoyl)-cyclopropanecarbonyl]-amino}-phenoxy)-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid as a white solid (0.048 g, 74% yield). MS (ESI) for C30H31F2N5O6Si: 624 (MH+).

Workup

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. washwashed with (2×) H2O (50 ml), 1M HCl (2×), sat'd NaCl (1×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9308a862361b41b5824adc0f59240ca6
Source dataset
uspto-grants-2011_07
Patent number
US07977345B2

Reaction notes

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