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Veratrylamine → 7-Chloro-5-(3,4-dimethoxybenzylamino)-2-(2-furyl)[1,2,4]triazolo[1,5-c]pyrimidine

HRID 1264871
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HRID 1264871 반응식
[Cl:1][C:2]1[N:7]=[C:6](SC)[N:5]2[C:10]([C:13]3[O:14][CH:15]=[CH:16][CH:17]=3)=[N:11][N:12]=[C:4]2[CH:3]=1.C1CCN2C(=NCCC2)CC1.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:34][NH2:35]>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:35][CH2:34][C:33]2[CH:36]=[CH:37][C:38]([O:39][CH3:40])=[C:31]([O:30][CH3:29])[CH:32]=2)[N:12]2[N:11]=[C:10]([C:13]3[O:14][CH:15]=[CH:16][CH:17]=3)[N:5]=[C:4]2[CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 79832VeratrylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 186137007-Chloro-3-(furan-2-yl)-5-(methylsulfanyl)[1,2,4]triazolo[4,3-c]pyrimidine

생성물 1

HCID 155243237-Chloro-5-(3,4-dimethoxybenzylamino)-2-(2-furyl)[1,2,4]triazolo[1,5-c]pyrimidine수율 74%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Into 600 mL of THF, 50.0 g (188 mmol) of Compound B was dissolved, and 42.0 mL (280 mmol) of DBU was added thereto, followed by stirring at room temperature for about 30 minutes. During the period, crystals were precipitated from the reaction solution. Next, 94 g (563 mmol) of 3,4-dimethoxybenzylamine was added thereto, followed by stirring at 60° C. for about 2 hours. After completion of the reaction, the solvent was evaporated, the residue was diluted with chloroform and washed with water, and the organic layer was dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was triturated with ethyl acetate to obtain 53.2 g of Compound D as a white solid (yield: 74%). The residue obtained by concentrating the solution part present after trituration was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to additionally recover Compound D in about 10% yield.

후처리

  1. customDuring the period, crystals were precipitated from the reaction solution
  2. stirringby stirring at 60° C. for about 2 hours
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated
  5. additionthe residue was diluted with chloroform
  6. washwashed with water
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe resulting residue was triturated with ethyl acetate

출처 및 근거

ORD 기록
ord-bd1ee6bcbfdf425789578eed8c3421dd
출처 데이터셋
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06545000B1

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