Sodium hydride → HCID 25061495, compound

HRID 2244089Notes

Reaction equation

HRID 2244089 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[CH2:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]=2[NH:4][CH:3]=1.[H-].[Na+].F[C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[N:22][C:23]([NH2:27])=[N:24]2)=[CH:19][CH:18]=1>CN(C)C=O>[NH2:27][C:23]1[N:22]=[CH:21][C:20]2[C:25](=[CH:26][C:17]([N:4]3[C:5]4[CH2:6][C:7]([CH3:13])([CH3:12])[CH2:8][C:9](=[O:11])[C:10]=4[C:2]([CH3:1])=[CH:3]3)=[CH:18][CH:19]=2)[N:24]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 104872107-Fluoroquinazolin-2-amineHCID 248207983,6,6-trimethyl-6,7-dihydro-1H-indol-4(5H)-one

Product 1

HCID 25061495HCID 25061495, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,6,6-Trimethyl-1,5,6,7-tetrahydro-indol-4-one (0.65 g, 3.68 mmol), sodium hydride (60% in oil, 0.177 g, 4.4 mmol), 7-fluoroquinazolin-2-amine (0.60 g, 3.68 mmol), and N,N-dimethylformamide are sealed in a microwave vessel and irradiated at 150 degrees Celsius for 1500 seconds. The mixture is purified by column chromatography and recrystallized from dichloromethane/hexane, affording 0.96 g of 1-(2-Amino-quinazolin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one (81%). LC/MS m/z=321 [M+H]+.

Workup

  1. customirradiated at 150 degrees Celsius for 1500 seconds
  2. customThe mixture is purified by column chromatography
  3. customrecrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-ace316acb0014da19a478ecc869b74fb
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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