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Chloride → 8-Methyl-6,7-dihydro-5H-cyclopenta[d][1,2,4]triazolo[-1,5-a]pyrimidine-2-carbaldehyde

HRID 638878
ノート
印刷プレビュー

反応式

HRID 638878 の反応式
CS(C)=O.[Cl-].[CH3:6][C:7]1[N:12]2[N:13]=[C:14]([CH2:16][OH:17])[N:15]=[C:11]2[N:10]=[C:9]2[CH2:18][CH2:19][CH2:20][C:8]=12.C(N(CC)CC)C>ClCCl.O>[CH3:6][C:7]1[N:12]2[N:13]=[C:14]([CH:16]=[O:17])[N:15]=[C:11]2[N:10]=[C:9]2[CH2:18][CH2:19][CH2:20][C:8]=12
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 312ChlorideHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 68701675(8-Methyl-6,7-dihydro-5H-cyclopenta[d][1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-methanol

生成物 1

HCID 222245208-Methyl-6,7-dihydro-5H-cyclopenta[d][1,2,4]triazolo[-1,5-a]pyrimidine-2-carbaldehyde収率 89%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 6344Dichloromethane溶媒4 回

反応条件

温度
23 °C

実験手順

To a round bottomed flask was loaded 0.17 ml of DMSO and 1 ml dichloromethane. The mixture was cooled to −50˜−60° C. Then a mixture of 0.1 ml oxallyl chloride and 2 ml dichloromethane was injected in into the flask all at once. The mixture was stirred at the same temperature for another 5 minutes. Then 0.174 grams of (8-Methyl-6,7-dihydro-5H-cyclopenta[d][1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-methanol in 2 ml dichloromethane was added within 2 minutes. The mixture was stirred at −50˜−60° C. for fifteen minutes and 0.7 ml triethylamine was next added. After another five minutes the reaction media was warmed up to 23° C. and a mixture of 20 ml water and 200 ml dichloromethane was added. The organic layer was dried over magnesium sulfate. Filter off the drying agent and concentrate the filtrate yielded 0.153 grams of product (89%). MS: 203.1 (M+H). H-NMR (CDCl3): δ 10.24 (s, 1H), 3.49 (m, 2H), 3.15 (m, 2H), 2.67 (s, 3H, CH3), 2.44 (m, 2H, CH2).

後処理

  1. customTo a round bottomed flask was loaded
  2. temperatureThe mixture was cooled to −50˜−60° C
  3. stirringThe mixture was stirred at −50˜−60° C. for fifteen minutes
  4. customAfter another five minutes the reaction media
  5. additionwas added
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationFilter off the drying agent
  8. concentrationconcentrate the filtrate

出典と根拠

ORDレコード
ord-2f959ba7c3d4446ebfb04dbb8944ba31
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07691842B2

反応ノート

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