Methyl iodide → HCID 21568182, compound

HRID 1579238Notes

Reaction equation

HRID 1579238 reaction equation
[H-].[Na+].[CH3:3]C(N(C)C)=O.[F:9][C:10]1[CH:28]=[CH:27][C:13]([CH2:14][N:15]2[C:20]3[N:21]=[CH:22][CH:23]=[CH:24][C:19]=3[C:18](=[O:25])[N:17]=[C:16]2[NH2:26])=[CH:12][CH:11]=1.CI>O>[F:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][N:15]2[C:20]3[N:21]=[CH:22][CH:23]=[CH:24][C:19]=3[C:18](=[O:25])[N:17]([CH3:3])[C:16]2=[NH:26])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 21568186HCID 21568186, compound

Product 1

HCID 21568182HCID 21568182, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 0.4 g. of sodium hydride in 60 ml. of dimethylacetamide is added 2.5 g. of 1-(4'-fluorobenzyl)-2-amino-pyrido[2,3-d]pyrimidin-4(1H)-one while maintaining the system under nitrogen. After stirring for one hour at room temperature, the mixture is treated by addition of 1.0 ml. of methyliodide. The resulting mixture is stirred at 20°C. for 15 hours. A small amount of water (ca 1.0 ml.) is then added and the mixture evaporated in vacuo. The residue is treated with ice/water and the resulting precipitate is recovered by filtering, washed with water and dried. The dried precipitate is then dissolved in methylene chloride, treated with charcoal and filtered through neutral alumina. The filtrate is concentrated in vacuo and ether added to obtain on crystallization 1-(4'-fluorobenzyl)-2,3-dihydro-2-imino-3-methyl-pyrido[2,3-d]pyrimidin-4(1H)-one

Workup

  1. additionTo a suspension of 0.4 g
  2. additionthe mixture is treated by addition of 1.0 ml
  3. stirringThe resulting mixture is stirred at 20°C. for 15 hours
  4. customthe mixture evaporated in vacuo
  5. additionThe residue is treated with ice/water
  6. customthe resulting precipitate is recovered
  7. filtrationby filtering
  8. washwashed with water
  9. customdried
  10. dissolutionThe dried precipitate is then dissolved in methylene chloride
  11. additiontreated with charcoal
  12. filtrationfiltered through neutral alumina
  13. concentrationThe filtrate is concentrated in vacuo and ether
  14. additionadded

Sources & evidence

ORD record
ord-27eb9fadb1db45998e7003090ab82796
Source dataset
uspto-grants-1976_01
Patent number
US03931178

Reaction notes

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