Tetrahydrofuran → HCID 68881362, compound

HRID 1785156Notes

Reaction equation

HRID 1785156 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[O:11]1C[CH2:14][CH2:13][CH2:12]1.Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31]Cl)=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1.[Cl:33][C:34]1[CH:42]=[C:41]([C:43]#[C:44][CH2:45][O:46][CH3:47])[C:37]2[O:38][CH2:39][O:40][C:36]=2[C:35]=1[NH2:48].[Cl-].[NH4+:50]>CN(C)C=O>[Cl:33][C:34]1[CH:42]=[C:41]([C:43]#[C:44][CH2:45][O:46][CH3:47])[C:37]2[O:38][CH2:39][O:40][C:36]=2[C:35]=1[NH:48][C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31][NH:50][CH2:14][CH2:13][CH2:12][OH:11])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 210827165-Chloro-7-(3-methoxyprop-1-ynyl)-1,3-benzodioxol-4-amineHCID 596829074-Chloro-7-(2-chloroethoxy)-6-methoxyquinazoline

Product 1

HCID 68881362HCID 68881362, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of sodium bis(trimethylsilyl)amide (5.6 ml) in tetrahydrofuran (1.0M, 5.6 mmol) was added dropwise to an ice-cold solution of 4-chloro-7-(2-chloroethoxy)-6-methoxyquinazoline (0.7 g, 2.6 mmol) and 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.675 g, 2.8 mmol) in dimethylformamide (8 ml). The mixture was allowed to warm to room temperature over 3 hours. 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. Flash chromatography on silica eluting with a mixture of 30-100% ethyl acetate in hexane gave the product as a solid. (0.608 g, 49%).

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
  5. additionFlash chromatography on silica eluting with a mixture of 30-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c68572d711c844ab8834df9b2d660fa7
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

Loading…