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 2362296ノート

反応式

HRID 2362296 の反応式
[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]

参加物

8

反応物 4

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

生成物 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 ester収率 56.9%

試薬・触媒・溶媒 3

HCID 1049Pyridine溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-80cbf3ef0c9c402c8333f7f328b046c9
出典データセット
uspto-grants-2014_04
特許番号
US08691826B2

反応ノート

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