Tetrabutylammonium Fluoride → HCID 59380192, compound

HRID 2353632Notes

Reaction equation

HRID 2353632 reaction equation
C[Si](C)(C(C)(C)C)[O:3][CH2:4][C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]2[CH3:17])[N:8]=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:19]=2)[N:6]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:28]([NH:27][C:25]([NH:24][C:21]1[CH:20]=[CH:19][C:18]([C:7]2[N:6]=[C:5]([CH2:4][OH:3])[CH:10]=[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]3[CH3:17])[N:8]=2)=[CH:23][CH:22]=1)=[O:26])[CH3:29]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59379944HCID 59379944, compound

Product 1

HCID 59380192HCID 59380192, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[4-[4-[(Dimethyl-tert-butyl-silyl)oxymethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-ethyl-urea (104 mg) was dissolved in THF (10 mL) and TBAF (1.0 M solution, 0.22 mL) was added. The reaction was allowed to stir for 1 hour at room temperature and then passed down a SCX-2 column. The column was washed with methanol and the desired material eluted with 7N ammonia in methanol. The fractions were concentrated in vacuo to give the desired compound (76 mg) as a white solid.

Workup

  1. washThe column was washed with methanol
  2. washthe desired material eluted with 7N ammonia in methanol
  3. concentrationThe fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-4805d8beee7848fd97e926d42522f739
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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