(Bis(2-methoxyethyl)amino)sulfur trifluoride → 3-((3R,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydro-2H-pyran-4-yl)-6-{[6-(fluoromethyl)pyridine-3-yl]methyl}benzo[h]quinazolin-4(3H)-one

HRID 82458Notes

Reaction equation

HRID 82458 reaction equation
[Si:1]([O:8][C@@H:9]1[C@@H:14]([N:15]2[C:24](=[O:25])[C:23]3[C:18](=[C:19]4[CH:38]=[CH:37][CH:36]=[CH:35][C:20]4=[C:21]([CH2:26][C:27]4[CH:28]=[N:29][C:30]([CH2:33]O)=[CH:31][CH:32]=4)[CH:22]=3)[N:17]=[CH:16]2)[CH2:13][CH2:12][O:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].COCCN(S(F)(F)[F:49])CCOC>ClCCl>[Si:1]([O:8][C@@H:9]1[C@@H:14]([N:15]2[C:24](=[O:25])[C:23]3[C:18](=[C:19]4[CH:38]=[CH:37][CH:36]=[CH:35][C:20]4=[C:21]([CH2:26][C:27]4[CH:28]=[N:29][C:30]([CH2:33][F:49])=[CH:31][CH:32]=4)[CH:22]=3)[N:17]=[CH:16]2)[CH2:13][CH2:12][O:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 679698743-((3R,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydro-2H-pyran-4-yl)-6-{[6-(hydroxymethyl)pyridine-3-yl]methyl}benzo[h]quinazolin-4(3H)-one

Product 1

HCID 679707123-((3R,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydro-2H-pyran-4-yl)-6-{[6-(fluoromethyl)pyridine-3-yl]methyl}benzo[h]quinazolin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-((3R,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydro-2H-pyran-4-yl)-6-{[6-(hydroxymethyl)pyridine-3-yl]methyl}benzo[h]quinazolin-4(3H)-one (Example 21, 0.035 g, 0.066 mmol) in 1 mL of dichloromethane at −78° C. was added [bis(2-methoxyethyl)amino]sulfur trifluoride (0.015 mL, 0.079 mmol). The reaction was warmed to rt, and after 3 h, the solution was purified via silica gel chromatography, eluting with 0-3% methanol in dichloromethane to provide 3-((3R,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydro-2H-pyran-4-yl)-6-{[6-(fluoromethyl)pyridine-3-yl]methyl}benzo[h]quinazolin-4(3H)-one that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 534.0 for [M+H]+.

Workup

  1. customthe solution was purified via silica gel chromatography
  2. washeluting with 0-3% methanol in dichloromethane

Sources & evidence

ORD record
ord-1d698bd286e24677af23a1c42f0ab06d
Source dataset
uspto-grants-2014_09
Patent number
US08846702B2

Reaction notes

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