Dimethylformamide dimethyl acetal → 1-(2', 6'-Dimethylphenyl)-4-[(2-pyridyl)methylamino]-1,2-dihydro-1,3,5-triazin-2-one

HRID 28059Notes

Reaction equation

HRID 28059 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([NH:12][C:13](=[NH:22])[NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)=[O:11].[CH3:23]N(C(OC)OC)C>CC#N>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[CH:23]=[N:22][C:13]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[N:12][C:10]1=[O:11]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178424815HCID 178424815, compound

Product 1

HCID 130393741-(2', 6'-Dimethylphenyl)-4-[(2-pyridyl)methylamino]-1,2-dihydro-1,3,5-triazin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 10.2 g. (28.0 mmol) of 1-(2',6'-dimethylphenyl)-3-[(2-pyridyl)methyl]amidinourea in CH3CN (100 ml) is added 10.0 g. (84.0 mmol) of DMF-DMA and the reaction mixture heated at reflux for two hours. The solvent is removed under vacuum and the residue diluted with H2O and made basic with 10% aqueous NaOH (pH10). The aqueous layer is extracted with CHCl3 (2×100 ml.) and the extracts dried (MgSO4) and concentrated under vacuum to an orange oil, which by NMR looks to be a mixture of starting material and product. The oil is layered out with H2O and Et2O. The oil solidifies. This solid is filtered and washed with H2O and Et2O and air dried. The solid is then crystallized (2×) from EtoAc to give 3.2 g. (37%) of tan crystalline solid, melting point 165°-6° C.

Workup

  1. additionTo a suspension of 10.2 g
  2. temperatureat reflux for two hours
  3. customThe solvent is removed under vacuum
  4. additionthe residue diluted with H2O
  5. extractionThe aqueous layer is extracted with CHCl3 (2×100 ml.)
  6. dry with materialthe extracts dried (MgSO4)
  7. concentrationconcentrated under vacuum to an orange oil, which by NMR
  8. additiona mixture of starting material and product
  9. filtrationThis solid is filtered
  10. washwashed with H2O and Et2O and air
  11. customdried
  12. customThe solid is then crystallized (2×) from EtoAc
  13. customto give 3.2 g

Sources & evidence

ORD record
ord-a42da8b118904051b39d4677e407634b
Source dataset
uspto-grants-1980_09
Patent number
US04225315

Reaction notes

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