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

HRID 728026노트

반응식

HRID 728026 반응식
[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

참가 물질

7

반응물 4

HCID 24386Thionyl Chloride2회HCID 11557703Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-CarboxylateHCID 224623842-Allyloxybenzamidine hydrochlorideHCID 135478883Ethyl 5-hydroxy-3-(methylthio)-1,2,4-triazine-6-carboxylate

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8471Triethylamine용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8e5aff8017bd4f6d8bbda98f2dc95b03
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05047404

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