Sodium hydride → HCID 25061752, compound

HRID 2244090Notes

Reaction equation

HRID 2244090 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]([C:21]([CH3:28])=[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]=[C:21]([CH3:28])[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 10374977HCID 10374977, compoundHCID 248207983,6,6-trimethyl-6,7-dihydro-1H-indol-4(5H)-one

Product 1

HCID 25061752HCID 25061752, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,6,6-Trimethyl-1,5,6,7-tetrahydro-indol-4-one (0.7 g, 4 mmol), sodium hydride (60% in oil, 0.20 g, 4.8 mmol), 7-Fluoro-4-methyl-quinazolin-2-ylamine (0.7 g, 4 mmol), and N,N-dimethylformamide are heated at 150 degrees Celsius for 2 h. The mixture is extracted with ethyl acetate/water. The organic layer is dried and concentrated. The residue is purified by column chromatography, affording 0.9 g of a solid 1-(2-Amino-4-methyl-quinazolin-7-yl)-3,6,6-trimethyl-1,5,6,7-tetrahydro-indol-4-one (68%). LC/MS m/z=335 [M+H]+.

Workup

  1. extractionThe mixture is extracted with ethyl acetate/water
  2. customThe organic layer is dried
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-6a29f4311da84a8baa7c9ffbc96bc71e
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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