Tetrabutylammonium Fluoride → HCID 58300158, compound

HRID 79182Notes

Reaction equation

HRID 79182 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]([NH:23][C:24]3[N:25]=[CH:26][C:27]4[C:32]5[CH:33]=[CH:34][N:35]=[C:36]([F:37])[C:31]=5[N:30]([CH:38]5[CH2:42][CH2:41][CH2:40][CH2:39]5)[C:28]=4[N:29]=3)=[N:21][CH:22]=2)[CH2:13][CH2:12]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:38]1([N:30]2[C:28]3[N:29]=[C:24]([NH:23][C:20]4[N:21]=[CH:22][C:17]([N:14]5[CH2:13][CH2:12][CH:11]([CH2:10][CH2:9][OH:8])[CH2:16][CH2:15]5)=[CH:18][CH:19]=4)[N:25]=[CH:26][C:27]=3[C:32]3[CH:33]=[CH:34][N:35]=[C:36]([F:37])[C:31]2=3)[CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58300008N-(5-(4-(2-((tert-butyl(dimethyl)silyl)oxy)ethyl)-1-piperidinyl)-2-pyridinyl)-9-cyclopentyl-8-fluoro-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine

Product 1

HCID 58300158HCID 58300158, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 294 (78 mg, 132 mop was dissolved in dry THF (3 mL). Tetrabutylammonium fluoride, 1.0M in THF (1.00 mL, 1.00 mmol) was added and the reaction stirred at room temperature for 4 hours. The solvent was removed in vacuo and silica gel chromatography (gradient elution hexanes+2.5%/0-100% ethyl acetate+2.5% TEA) afforded compound 291 as a beige solid (44 mg, 70%). 1H NMR (500 MHz, DMSO-d6) δ 11.60-11.85 (m, 2 H) 9.49 (s, 2 H) 8.19-8.24 (m, 2 H) 8.13-8.19 (m, 2 H) 8.05-8.10 (m, 2 H) 7.96-8.04 (m, 2 H) 7.61-7.71 (m, 2 H) 5.48 (s, 1 H) 3.64 (d, J=11.98 Hz, 2 H) 3.44 (t, J=6.48 Hz, 2 H) 2.71-2.90 (m, 2 H) 2.20 (br. s., 2 H) 2.09 (br. s., 2 H) 2.00 (br. s., 2 H) 1.66-1.82 (m, 4 H) 1.52-1.66 (m, 1 H) 1.37 (d, J=6.60 Hz, 2 H) 1.28 (none, 2 H) ppm.

Workup

  1. customThe solvent was removed in vacuo and silica gel chromatography (gradient elution hexanes+2.5%/0-100% ethyl acetate+2.5% TEA)

Sources & evidence

ORD record
ord-49ce65021af14ab78231a52ce558e5c3
Source dataset
uspto-grants-2014_09
Patent number
US08841312B2

Reaction notes

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