Tetrabutylammonium Fluoride → HCID 178519966, compound

HRID 2169332Notes

Reaction equation

HRID 2169332 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:41]1[CH2:44][O:43][CH2:42]1)[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:34][CH2:33][CH2:32][CH2:31]2)[N:15]=1)=[O:13])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]([CH:41]1[CH2:44][O:43][CH2:42]1)[C:12]([C:14]1[C:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:18]([OH:28])[N:17]=[C:16]([CH2:29][C:30]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:31][CH2:32][CH2:33][CH2:34]2)[N:15]=1)=[O:13]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455276HCID 178455276, compound

Product 1

HCID 178519966HCID 178519966, compoundYield 76.68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-oxetan-3-yl-amide (296) (240 mg, 0.39 mmol) in tetrahydrofuran (20 mL) was added a 1M solution of tetrabutylammoniumfluorid in tetrahydrofuran (1.2 mL, 1.16 mmol) at room temperature and stirring was continued for 60 min at room temperature. After completion of the reaction, the reaction mixture was concentrated and the residue purified by Combi-Flash column (eluted at 5% methanol in dichloromethane) to get 5-Benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-oxetan-3-yl-amide (297) as an off-white sticky solid (150 mg, 76.68%).

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue purified by Combi-Flash column (eluted at 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a330f7bcf7d24a4d8eabe2e8599c18be
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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