Sodium hydride → HCID 10690257, compound

HRID 1886074Notes

Reaction equation

HRID 1886074 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:5]=[C:6]([CH3:15])[C:7]2[C:8](=[N:10][C:11](=[O:14])[CH2:12][CH:13]=2)[N:9]=1.Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[C:26]#[N:27])=[CH:20][CH:19]=1>CN(C=O)C>[CH3:3][C:4]1[N:5]=[C:6]([CH3:15])[C:7]2[CH:13]=[CH:12][C:11](=[O:14])[N:10]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([C:24]4[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=4[C:26]#[N:27])=[CH:22][CH:23]=3)[C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 67696840HCID 67696840, compound

Product 1

HCID 10690257HCID 10690257, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Using the same procedure as described in Step 1 of Example 8, to a stirred suspension of NaH (60% dispersion in mineral oil) in DMF add 2,4-dimethyl-7H-pyrido[2,3-d]pyrimidin-7-one, prepared according to T. Sakamoto, et al. Chem. Pharm. Bull., 1982, 30, 2410. After 45 min, add 2-[4-(bromomethyl)phenyl]benzonitrile in DMF and stir the mixture at room temperature for 18 h. Add water and extract the mixture with CH2Cl2. Concentrate the extracts and purify the crude product by flash chromatography (2% MeOH/CH2Cl2). Trituration with ether gives the product.

Workup

  1. customprepared
  2. extractionAdd water and extract the mixture with CH2Cl2
  3. concentrationConcentrate the extracts
  4. custompurify the crude product by flash chromatography (2% MeOH/CH2Cl2)
  5. customTrituration with ether gives the product

Sources & evidence

ORD record
ord-8dc30d9dbc0b43d2a502d6db52c0c6df
Source dataset
uspto-grants-1992_09
Patent number
US05149699

Reaction notes

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