Tetrabutylammonium Fluoride → [3-[2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-6-yl]-methanol

HRID 1435045Notes

Reaction equation

HRID 1435045 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[CH:13][N:14]2[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[CH:10][CH:9]=1)(C)(C)C.Cl[C:28]1[CH:33]=[CH:32][N:31]=[C:30]([NH:34][CH:35]2[CH2:40][C:39]([CH3:42])([CH3:41])[NH:38][C:37]([CH3:44])([CH3:43])[CH2:36]2)[N:29]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[CH3:41][C:39]1([CH3:42])[CH2:40][CH:35]([NH:34][C:30]2[N:29]=[C:28]([C:12]3[C:11]4[C:15](=[CH:16][C:8]([CH2:7][OH:6])=[CH:9][CH:10]=4)[N:14]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[CH:13]=3)[CH:33]=[CH:32][N:31]=2)[CH2:36][C:37]([CH3:44])([CH3:43])[NH:38]1

Participants

4

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 57936167(4-Chloro-pyrimidin-2-yl)(2,2,6,6-tetramethyl-piperidin-4-yl)-amineHCID 1317277522-[[6-(2-Tert-butylsilyloxypropan-2-yl)indol-1-yl]methoxy]ethyl-trimethylsilane

Product 1

HCID 57936184[3-[2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-6-yl]-methanol

Procedure

[3-[2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-6-yl]-methanol was prepared as described in Example 215, starting from 6-(tert-butyl-dimethyl-silanyloxymethyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole and (4-chloro-pyrimidin-2-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine, followed by selective cleavage of the TBDMS-protecting group with TBAF. Yield: 7.1 g (93%).

Sources & evidence

ORD record
ord-2e26fbab360140fbb2ddb0a45631e824
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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