Methyl iodide → N-(4-Methoxyphenyl)-N-methyl-4-(3-pyridinyl)-2-pyrimidinamine

HRID 2352172Notes

Reaction equation

HRID 2352172 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:24]I>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]([CH3:24])[C:10]2[N:15]=[C:14]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:13]=[CH:12][N:11]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14346975N-(4-Methoxyphenyl)-4-(pyridin-3-yl)pyrimidin-2-amine

Product 1

HCID 14722206N-(4-Methoxyphenyl)-N-methyl-4-(3-pyridinyl)-2-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 2.78 g portion of N-(4-methoxyphenyl)-4-(3-pyridinyl)-2-pyrimidinamine was dissolved in 30 ml of dimethylformamide. A 528 mg portion of sodium hydride (50% in oil) was added, the reaction sealed and stirred for 45 minutes. A solution of 1.70 g of methyl iodide in 2 ml of dimethylformamide was added, the sealed mixture was stirred overnight and the solvent removed. The residue was partitioned between water and chloroform. The organic phase was dried, filtered and evaporated. The residue was crystallized from ether-hexane giving 1.4 g of the desired product as yellow crystals, mp 88°-90° C.

Workup

  1. customthe reaction sealed
  2. stirringthe sealed mixture was stirred overnight
  3. customthe solvent removed
  4. customThe residue was partitioned between water and chloroform
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from ether-hexane giving 1.4 g of the desired product as yellow crystals, mp 88°-90° C.

Sources & evidence

ORD record
ord-7ca9f3a2f3af478dbca59f954336f613
Source dataset
uspto-grants-1989_10
Patent number
US04876252

Reaction notes

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