Thionyl Chloride → 3-Methylthio-8-oxo-6-(2-allyloxyphenyl)-7,8-dihydropyrimido[4,5-e][1,2,4]triazine

HRID 728026Notes

Reaction equation

HRID 728026 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.CSC1NC(=O)C(C(OCC)=O)=NN=1.S(Cl)(Cl)=O.Cl.[CH2:34]([O:37][C:38]1[CH:46]=[CH:45][CH:44]=[CH:43][C:39]=1[C:40]([NH2:42])=[NH:41])[CH:35]=[CH2:36]>C(#N)C.C(N(CC)CC)C>[CH3:1][S:2][C:3]1[N:4]=[N:5][C:6]2[C:10](=[O:12])[NH:42][C:40]([C:39]3[CH:43]=[CH:44][CH:45]=[CH:46][C:38]=3[O:37][CH2:34][CH:35]=[CH2:36])=[N:41][C:7]=2[N:8]=1

Participants

7

Reactant 4

HCID 24386Thionyl Chloride2×HCID 11557703Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-CarboxylateHCID 22462384HCID 22462384, compoundHCID 135478883Ethyl 3-(methylsulfanyl)-5-oxo-2,5-dihydro-1,2,4-triazine-6-carboxylate

Product 1

HCID 1356708043-Methylthio-8-oxo-6-(2-allyloxyphenyl)-7,8-dihydropyrimido[4,5-e][1,2,4]triazine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

A cooled (5° C.) solution of 3-methylthio-5-chloro-6-carboethoxy-1,2,4-triazine (prepared by heating 3-methylthio-5-oxo-6-carboethoxy-4,5-dihydro-1,2,4-triazine, 1.5 g, with thionyl chloride, 30 ml, under reflux for two hours and thereafter removing thionyl chloride) in acetonitrile (30 ml) was added to a cooled stirred mixture of 2-allyloxybenzamidine hydrochloride (2.23 g) and triethylamine (1.06 g) in acetonitrile (50 ml). The mixture was stirred with cooling (0°-5° C.) for 15 minutes, then more triethylamine (0.71 g) was added and the reaction mixture was stirred at ambient temperature for two hours and left standing overnight. A yellow precipitate was collected, washed with water and recrystallised from acetonitrile and then from acetonitrile/ethanol (50%) to afford the title compound, 0.35 g, m.p. 238°-239° C.

Workup

  1. customprepared
  2. stirringThe mixture was stirred
  3. temperaturewith cooling (0°-5° C.) for 15 minutes
  4. stirringthe reaction mixture was stirred at ambient temperature for two hours
  5. waitleft
  6. customA yellow precipitate was collected
  7. washwashed with water
  8. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-8e5aff8017bd4f6d8bbda98f2dc95b03
Source dataset
uspto-grants-1991_09
Patent number
US05047404

Reaction notes

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