Tetrabutylammonium Fluoride → HCID 11282450, compound

HRID 1434940Notes

Reaction equation

HRID 1434940 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)[N:3]=1.C([Si](C)(C)[O:24][CH:25]([C:40]1[S:41][CH:42]=[CH:43][CH:44]=1)[C:26]([F:39])([F:38])[C:27]([O:30][Si](C(C)(C)C)(C)C)([CH3:29])[CH3:28])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:39][C:26]([F:38])([C:27]([CH3:28])([OH:30])[CH3:29])[CH:25]([C:40]1[S:41][C:42]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]3[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]3)[N:3]=2)=[CH:43][CH:44]=1)[OH:24]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 57936167(4-Chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amineHCID 69068572HCID 69068572, compound

Product 1

HCID 11282450HCID 11282450, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared analogous to Method C, starting from (4-chloro-pyrimidin-2-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine and 2-[1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-2,2-difluoro-3-methyl-butyl]-thiophene (prepared from 2,2-Difluoro-3-hydroxy-3-thiophen-2-yl-propionic acid ethyl ester by treatment with MeMgBr (Step A of Method A) and TBDMS protection), followed by TBDMS cleavage with TBAF in THF.

Sources & evidence

ORD record
ord-e5d70582ab8e4e9e97011eaac6b657f4
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

Loading…