Sodium hydride → 8-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine

HRID 732080ノート

反応式

HRID 732080 の反応式
[H-].[Na+].[N:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]3[CH2:14][CH2:15][CH2:16][NH:17][C:12]3=[N:11][N:10]=2)=[CH:5][CH:4]=1.[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[O:29][N:28]=[C:27]([CH2:30]Cl)[N:26]=2)[CH:22]=[CH:23][CH:24]=1>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]([C:25]2[O:29][N:28]=[C:27]([CH2:30][N:17]3[CH2:16][CH2:15][CH2:14][N:13]4[C:9]([C:6]5[CH:7]=[CH:8][N:3]=[CH:4][CH:5]=5)=[N:10][N:11]=[C:12]34)[N:26]=2)[CH:22]=[CH:23][CH:24]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 100825203-(Chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazoleHCID 1361179203-Pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine

生成物 1

HCID 670707678-[5-(3-Chloro-phenyl)-[1,2,4]oxadiazol-3-ylmethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine収率 32.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

32 mg (1.31 mmol) NaH was added to a solution of 193 mg (0.96 mmol) 3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrimidine in 10 ml DMF at room temperature. After 10 min 200 mg (0.87mmol) 5-(3-chloro-phenyl)-3-chloromethyl-[1,2,4]oxadiazole was added to the reaction mixture. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with NH4Cl(sat) and extracted twice with EtOAc. The combined organic phases were washed with water, dried and concentrated. Flashchromatography (CH2Cl2/MeOH 20:1) afforded 111 mg (32%) of a white solid. 1H NMR (CDCl3), d (ppm): 2.24 (m, 2 H), 3.57 (m, 2 H) 4.15 (m, 2 H) 5.01 (s, 2 H) 7.46 (t, 1 H) 7.56 (d, 1 H) 7.62 (d, 2 H) 7.99 (d, 1 H) 8.10 (s, 1 H) 8.70 (d, 2 H).

後処理

  1. extractionextracted twice with EtOAc
  2. washThe combined organic phases were washed with water
  3. customdried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-fdaa5fd19621477394410c05126284b4
出典データセット
uspto-grants-2009_09
特許番号
US07585881B2

反応ノート

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