Tetrahydrofuran → HCID 68881822, compound

HRID 1785153Notes

Reaction equation

HRID 1785153 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].O1CCCC1.Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][Cl:34])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1.[Cl:35][C:36]1[CH:44]=[C:43]([C:45]#[C:46][CH2:47][O:48][CH3:49])[C:39]2[O:40][CH2:41][O:42][C:38]=2[C:37]=1[NH2:50].[Cl-].[NH4+]>CN(C)C=O>[Cl:34][CH2:33][CH2:32][CH2:31][CH2:30][O:29][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([NH:50][C:37]3[C:38]4[O:42][CH2:41][O:40][C:39]=4[C:43]([C:45]#[C:46][CH2:47][O:48][CH3:49])=[CH:44][C:36]=3[Cl:35])=[N:18][CH:19]=[N:20]2)=[CH:25][C:24]=1[O:27][CH3:28]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 210827165-Chloro-7-(3-methoxyprop-1-ynyl)-1,3-benzodioxol-4-amineHCID 85912885HCID 85912885, compound

Product 1

HCID 68881822HCID 68881822, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of sodium bis(trimethylsilyl)amide (2.66 ml) in tetrahydrofuran (1.0M, 2.66 mmol) was added dropwise to an ice-cold solution of 4-chloro-7-(4-chlorobutoxy)-6-methoxyquinazoline (0.4 g, 1.33 mmol) and 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.35 g, 1.47 mmol) in dimethylformamide (4 ml). The mixture was allowed to warm to room temperature over 1 hour. A saturated solution of ammonium chloride was added and the mixture was partitioned between water and dichloromethane. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure to give 7-(4-chlorobutoxy)-N-[5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]-6-methoxyquinazolin-4-amine as a gum (0.493 g, 73%). NMR Spectrum: (CDCl3) 2.05 (m, 4H), 3.48 (s, 3H), 3.65 (t, 2H), 3.98 (s, 3H), 4.23 (t, 2H), 4.37 (s, 2H), 6.08 (s, 2H), 6.88 (s, 1H), 7.07 (s, 1H), 7.09 (s, 1H), 7.25 (s, 1H), 8.63 (s, 1H). Mass Spectrum: M+H+ 504 and M+H− 502.

Workup

  1. customthe mixture was partitioned between water and dichloromethane
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7be5ce8be65f47ca928b7c5a651b2dba
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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