Tetrahydrofuran → HCID 68881307, compound

HRID 1785158Notes

Reaction equation

HRID 1785158 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][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1.[Cl:31][C:32]1[CH:40]=[C:39]([C:41]#[C:42][CH2:43][O:44][CH3:45])[C:35]2[O:36][CH2:37][O:38][C:34]=2[C:33]=1[NH2:46].[Cl-].[NH4+]>CN(C)C=O>[Cl:31][C:32]1[CH:40]=[C:39]([C:41]#[C:42][CH2:43][O:44][CH3:45])[C:35]2[O:36][CH2:37][O:38][C:34]=2[C:33]=1[NH:46][C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH3:30])=[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 27693644-Chloro-6,7-dimethoxyquinazolineHCID 210827165-Chloro-7-(3-methoxyprop-1-ynyl)-1,3-benzodioxol-4-amine

Product 1

HCID 68881307HCID 68881307, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of sodium bis(trimethylsilyl)amide (1.5 ml) in tetrahydrofuran (1.0M, 1.5 mmol) was added dropwise to an ice-cold solution of 4-chloro-6,7-dimethoxyquinazoline (0.15 g, 0.7 mmol) and 5-chloro-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.176 g, 0.7 mmol) in dimethylformamide (4 ml). The mixture was allowed to warm to room temperature over 2 hours. A saturated solution of ammonium chloride was added and the mixture was partitioned between water and dichloromethane. The organic layer was separated, washed with a saturated solution of sodium chloride, dried over magnesium sulfate and evaporated under reduced pressure. Flash chromatography on silica eluting with a mixture of 3-10% methanol in dichloromethane gave the product as a solid (0.118 g, 60%).

Workup

  1. customthe mixture was partitioned between water and dichloromethane
  2. customThe organic layer was separated
  3. washwashed with a saturated solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. additionFlash chromatography on silica eluting with a mixture of 3-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-a2ea710336cc4b5e82dfc827cf25ab1c
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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