Sodium bis(trimethylsilyl)amide → HCID 68880977, compound

HRID 1785129Notes

Reaction equation

HRID 1785129 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:16][C:17]1[C:22]2[O:23][CH2:24][O:25][C:21]=2[C:20]([C:26]#[C:27][CH2:28][NH:29][C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[CH:19][C:18]=1[Cl:35].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CN(C=O)C>[Cl:35][C:18]1[CH:19]=[C:20]([C:26]#[C:27][CH2:28][NH:29][C:30](=[O:34])[N:31]([CH3:32])[CH3:33])[C:21]2[O:25][CH2:24][O:23][C:22]=2[C:17]=1[NH:16][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 68881428HCID 68881428, compound

Product 1

HCID 68880977HCID 68880977, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This was prepared using the method described in example 4 using 4-chloro-6,7-dimethoxyquinazoline (160 mg, 0.71 mmol), N′-[3-(7-amino-6-chloro-1,3-benzodioxol-4-yl)prop-2-yn-1-yl]-N,N-dimethylurea (232 mg, 0.78 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 1.5 ml) in DMF (3 ml). The crude product was purified by column chromatography on silica using increasing concentrations of methanol in dichloromethane as eluent. There was thus obtained the title compound (265 mg, 77%) as a pale brown solid; NMR Spectrum:DMSOd6) 2.81 (s, 6H), 3.91 (s, 3H), 3.92 (s, 3H), 4.09 (d, 2H), 6.14 (s, 2H), 6.82 (t, 1H), 7.07 (s, 1H), 7.18 (s, 1H), 7.82 (s, 1H), 8.33 (s, 1H), 9.47 (s, 1H); Mass Spectrum: M+H+ 484/486.

Workup

  1. customThis was prepared
  2. customThe crude product was purified by column chromatography on silica using
  3. temperatureincreasing concentrations of methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-dfa75bdb4e6845028a04bef467c823d7
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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