Sodium bis(trimethylsilyl)amide → N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amine

HRID 1785137Notes

Reaction equation

HRID 1785137 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][Cl:18])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Cl:19][C:20]1[CH:28]=[C:27]([C:29]#[C:30][CH2:31][O:32][CH3:33])[C:23]2[O:24][CH2:25][O:26][C:22]=2[C:21]=1[NH2:34].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CN(C=O)C>[Cl:19][C:20]1[CH:28]=[C:27]([C:29]#[C:30][CH2:31][O:32][CH3:33])[C:23]2[O:24][CH2:25][O:26][C:22]=2[C:21]=1[NH:34][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][Cl:18])=[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 210827165-Chloro-7-(3-methoxyprop-1-ynyl)-1,3-benzodioxol-4-amineHCID 574472274-Chloro-7-(3-chloropropoxy)-6-methoxyquinazoline

Product 1

HCID 68882624N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-7-(3-chloropropoxy)-6-methoxyquinazolin-4-amineYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This was prepared using the method described in example 4 using 4-chloro-7-(3-chloropropoxy)-6-methoxyquinazoline (400 mg, 1.39 mmol), 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (367 mg, 1.53 mmol) and sodium bis(trimethylsilyl)amide (1.0M in THF, 2.90 ml) in DMF (3 ml). The crude product was purified by column chromatography on silica using ethyl acetate as eluent. There was thus obtained the title compound (454 mg, 66%) as a pale yellow solid; NMR Spectrum:(CDCl3) 2.39 (quintet, 2H), 3.46 (s, 3H), 3.79 (t, 2H), 3.98 (s, 3H), 4.33 (t, 2H), 4.35 (s, 2H), 6.07 (s, 2H), 6.94 (s, 1H), 7.07 (s, 1H), 7.10 (s, 1H), 7.29 (s, 1H), 8.63 (s, 1H); Mass Spectrum: M+H+ 490.

Workup

  1. customThis was prepared
  2. customThe crude product was purified by column chromatography on silica

Sources & evidence

ORD record
ord-0dc265fd3757472a978addaf18056d89
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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