Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-Carboxylate → 3-Methylthio-8-oxo-6-(2-isobutoxyphenyl)-7,8-dihydropyrimido[4,5-e][1,2,4]triazine

HRID 1936692Notes

Reaction equation

HRID 1936692 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[N:5][C:6]([C:10]([O:12]CC)=O)=[C:7](Cl)[N:8]=1.Cl.[CH2:16]([O:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([NH2:25])=[NH:24])[CH:17]([CH3:19])[CH3:18]>C(N(CC)CC)C>[CH3:1][S:2][C:3]1[N:4]=[N:5][C:6]2[C:10](=[O:12])[NH:25][C:23]([C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[O:20][CH2:16][CH:17]([CH3:19])[CH3:18])=[N:24][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 11557703Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-CarboxylateHCID 224623702-Isobutoxybenzamidine hydrochloride

Product 1

HCID 1356708053-Methylthio-8-oxo-6-(2-isobutoxyphenyl)-7,8-dihydropyrimido[4,5-e][1,2,4]triazine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a similar manner to Example 85 reaction of 3-methylthio-5-chloro-6-carboethoxy-1,2,4-triazine (prepared from 3-methylthio-5-oxo-6-carboethoxy-4,5-dihydro-1,2,4-triazine, 1.5 g) with 2-isobutoxybenzamidine hydrochloride (2.37 g) and triethylamine (1.75 g) afforded the crude title compound (1.71 g). This was recrystallized from acetonitrile, then dissolved in chloroform, the organic solution was washed with 2 Normal hydrochloric acid (×2), chloroform removed under reduced pressure and the residue recrystallized twice from ethanol to afford the title compound, 0.32 g, m.p. 237-238° C.

Workup

  1. customafforded the crude title compound (1.71 g)
  2. customThis was recrystallized from acetonitrile
  3. dissolutiondissolved in chloroform
  4. washthe organic solution was washed with 2 Normal hydrochloric acid (×2), chloroform
  5. customremoved under reduced pressure
  6. customthe residue recrystallized twice from ethanol

Sources & evidence

ORD record
ord-fb01623046f74a0b8e5a6d8506884260
Source dataset
uspto-grants-2002_05
Patent number
US06391885B1

Reaction notes

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