Sodium hydride → HCID 54086185, compound

HRID 2300068Notes

Reaction equation

HRID 2300068 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH2:14]([NH:16][C:17]1[C:22]([CH:23]=O)=[CH:21][N:20]=[C:19]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:18]=1)[CH3:15]>CN(C)C=O>[CH2:14]([NH:16][C:17]1[C:22]([CH:23]=[CH:5][C:3]#[N:4])=[CH:21][N:20]=[C:19]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:18]=1)[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 75676Diethyl (cyanomethyl)phosphonateHCID 108240804-Ethylamino-2-phenylamino-pyrimidine-5-carbaldehyde

Product 1

HCID 54086185HCID 54086185, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a room temperature suspension of sodium hydride (38 mg of a 60% suspension of NaH in oil) in 5 mL of dimethylformamide was added diethyl cyanomethylphosphonate (150 μL, 0.93 mmol). The reaction mixture was stirred at room temperature for 15 minutes, then 4-ethylamino-2-phenylamino-pyrimidine-5-carbaldeyde (200 mg, 0.83 mmol) in 2 mL of dimethylformamide was added, and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was partitioned between brine and ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo The residue was purified by flash chromatography eluting with 1:1 ethyl acetate:hexane. The fractions containing product were concentrated, and hexane was added to the residue. The resultant solid was collected by filtration to give 91 mg (43%) of 3-(4-ethylamino-2-phenylamino-pyrimidin-5-yl)acrylonitrile, mp 244-246° C. Concentration of the filtrate provided an additional 68 mg (32%) of product.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 minutes
  2. customThe reaction mixture was partitioned between brine and ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo The residue
  6. customwas purified by flash chromatography
  7. washeluting with 1:1 ethyl acetate
  8. additionThe fractions containing product
  9. concentrationwere concentrated
  10. additionhexane was added to the residue
  11. filtrationThe resultant solid was collected by filtration

Sources & evidence

ORD record
ord-8962ef1fd4af43fab4a960ce58513e1b
Source dataset
uspto-grants-2002_12
Patent number
US06498163B1

Reaction notes

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