Hexane → HCID 178519959, compound

HRID 2169397Notes

Reaction equation

HRID 2169397 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH:45]1[CH2:48][O:47][CH2:46]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[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[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.C(OCC)(=O)C.CCCCCC>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]([CH:45]1[CH2:46][O:47][CH2:48]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[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37][CH:36]=3)[CH2:31][CH2:32][CH2:33][CH2:34]2)[N:15]=1)=[O:13]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 178455271HCID 178455271, compound

Product 1

HCID 178519959HCID 178519959, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-oxetan-3-yl-amide (362) (290 mg, 0.43 mmol) in tetrahydrofuran (10 mL) was added tetrabutylammoniumfluorid (1M in tetrahydrofuran, 1.3 mL, 13 mmol) at 0° C. and the reaction mixture was stirred at room temperature for 1.5 h (silica TLC, ethyl acetate:hexane=1:1/SiO2/UV, Rf=0.3.) The tetrahydrofuran was removed in vacuum and the crude mass was diluted with ethyl acetate (50 mL) and washed with water (25 mL) and brine (25 mL). The organic phase was thereafter dried and concentrated in vacuum to get a crude mass which was purified by CombiFlash using a gradient eluent mixture of ethyl acetate and hexane to obtain pure 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-oxetan-3-yl-amide (363) (175 mg, 73%) as a white solid.

Workup

  1. customwas removed in vacuum
  2. additionthe crude mass was diluted with ethyl acetate (50 mL)
  3. washwashed with water (25 mL) and brine (25 mL)
  4. customThe organic phase was thereafter dried
  5. concentrationconcentrated in vacuum
  6. customto get a crude mass which
  7. customwas purified by CombiFlash
  8. additiona gradient eluent mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-f54893f6170e48a392a83c725a32920f
Source dataset
uspto-grants-2015_06
Patent number
US09045486B2

Reaction notes

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