Diisopropylethylamine → 2-Allyl-5-(4-cyanophenyl)-7-methyl-3-oxo-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylic acid methyl ester

HRID 570869노트

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HRID 570869 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:7]=[C:8](OC)[NH:9][C:10]=1[CH3:11])=[O:4].Cl[C:23](OC1C=CC([N+]([O-])=O)=CC=1)=[O:24].Cl.[CH2:36]([NH:39][NH2:40])[CH:37]=[CH2:38].CCN(C(C)C)C(C)C>C(Cl)Cl.N1C=CC=CC=1.CC#N>[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:14]2[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=2)[N:7]2[C:23](=[O:24])[N:39]([CH2:36][CH:37]=[CH2:38])[N:40]=[C:8]2[NH:9][C:10]=1[CH3:11])=[O:4]

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 171127Allylhydrazine hydrochlorideHCID 674375874-(4-Cyanophenyl)-2-methoxy-6-methyl-1,4-dihydropyrimidine-5-carboxylic acid methyl ester

생성물 1

HCID 1363595122-Allyl-5-(4-cyanophenyl)-7-methyl-3-oxo-2,3,5,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine-6-carboxylic acid methyl ester수율 56.9%

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

Intermediate 4 (1.42 g, 5 mmol) was dissolved in a mixture of DCM (10 mL) and pyridine (10 mL) and cooled using an ice bath. A solution of 4-nitrophenyl chloroformate (0.955 mg, 4.75 mmol) in DCM (10 mL) was added dropwise, and the resulting solution was stirred at 0° C. for 1.5 hours, and then a solution of allyl hydrazine hydrochloride (1.0 g, 5.5 mmol) and DIPEA (3.75 mL, 22 mmol) in CH3CN (10 mL) was added in one portion. The resulting mixture was allowed to warm to RT, stirred for 4 hours, and then partitioned between EtOAc and water. The organic layer was separated, washed with water, followed by brine, then dried (Na2SO4) and evaporated in vacuo to yield the title compound as a yellow oil (0.95 g).

후처리

  1. temperaturecooled
  2. temperatureto warm to RT
  3. stirringstirred for 4 hours
  4. custompartitioned between EtOAc and water
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-18faef08bed543908b2ad9155e659056
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023855B2

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