Water → HCID 11592167, compound

HRID 2267343Notes

Reaction equation

HRID 2267343 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[CH:60]=[CH:59][C:23]([CH2:24][C:25]2[S:29][C:28]([C:30]3[C:35]([Br:36])=[CH:34][N:33]=[C:32]([NH:37][CH2:38][CH2:39][N:40]4[C:44]([CH3:46])([CH3:45])[C:43](=[O:47])[NH:42][C:41]4=[O:48])[N:31]=3)=[CH:27][C:26]=2[CH2:49][CH2:50][O:51][Si](C(C)(C)C)(C)C)=[CH:22][CH:21]=1.O>O1CCCC1>[F:19][C:20]1[CH:60]=[CH:59][C:23]([CH2:24][C:25]2[S:29][C:28]([C:30]3[C:35]([Br:36])=[CH:34][N:33]=[C:32]([NH:37][CH2:38][CH2:39][N:40]4[C:44]([CH3:46])([CH3:45])[C:43](=[O:47])[NH:42][C:41]4=[O:48])[N:31]=3)=[CH:27][C:26]=2[CH2:49][CH2:50][OH:51])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 60204456HCID 60204456, compound

Product 1

HCID 11592167HCID 11592167, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (5 mL, 1M in tetrahydrofuran, 5.00 mmol) was added slowly to a solution of 1-(2-(4-(5-(4-fluorobenzyl)-4-(2-(tert-butyldimethylsilyloxy)ethyl)thiophen-2-yl)-5-bromopyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione (1.8 g, 2.66 mmol) in tetrahydrofuran (40 mL) at rt. After stirring at rt for 4 h, 100 mL of water was added. The mixture was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the product purified by flash chromatography eluting with methanol/dichloromethane (1:30) to give the title compound as a slightly yellow solid (1.2 g, 80%). MS (M+H)+ 562/564.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo
  6. customthe product purified by flash chromatography
  7. washeluting with methanol/dichloromethane (1:30)

Sources & evidence

ORD record
ord-eb3c038080054d228fc8d7f0d41e9fb6
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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