Sodium periodate → 6-(4-Methoxybenzyl)-5-oxo-5,6-dihydropyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-9-carbaldehyde

HRID 926117

反応式

HRID 926117 の反応式
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[C:13]3[N:14]=[CH:15][C:16]([CH:18]=C)=[CH:17][C:12]=3[C:11]3=[N:20][CH:21]=[N:22][N:10]3[C:9]2=[O:23])=[CH:5][CH:4]=1.I([O-])(=O)(=O)=[O:27].[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O.C(O)CCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:13]3[N:14]=[CH:15][C:16]([CH:18]=[O:27])=[CH:17][C:12]=3[C:11]3=[N:20][CH:21]=[N:22][N:10]3[C:9]2=[O:23])=[CH:24][CH:25]=1

参加物

7

反応物 2

HCID 23667635Sodium periodateHCID 867053866-(4-methoxybenzyl)-9-vinylpyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

生成物 1

HCID 867053916-(4-Methoxybenzyl)-5-oxo-5,6-dihydropyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine-9-carbaldehyde収率 103.5%

試薬・触媒・溶媒 4

HCID 2631-Butanol触媒HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

6-(4-Methoxybenzyl)-9-vinylpyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (Example 30, 3.96 g, 11.9 mmol) was suspended in THF (80 mL) and heated with a heat gun to effect dissolution. Similarly, sodium periodate (5.84 g, 27.3 mmol) was heated in water (40 mL) to effect dissolution. The above solutions were combined with vigorous stirring. While the stirred mixture was still at 40° C., osmium(VIII) oxide in ten-butanol (2.90 mL, 2.5%, 0.30 mmol) was added and the mixture was stirred vigorously for 4 h. The reaction mixture was diluted with water (300 mL) and extracted with EtOAc (3×150 mL) and DCM (3×150 mL). The combined organic layers were dried (MgSO4) and concentrated to afford the title compound (4.13 g, 99%) as a black solid which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 3.77 (s, 3H), 5.80 (s, 2H), 6.83 (d, J=8.66 Hz, 2H), 7.61 (d, J=8.66 Hz, 2H), 8.41 (s, 1H), 9.10 (d, J=2.13 Hz, 1H), 9.26 (d, J=2.13 Hz, 1H), 10.21 (s, 1H). [M+H]=336.2.

後処理

  1. temperatureheated with a heat gun
  2. dissolutiondissolution
  3. dissolutiondissolution
  4. customwas still at 40° C.
  5. extractionextracted with EtOAc (3×150 mL) and DCM (3×150 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-0b8ef88e693e469ca7430edbe01e4957
出典データセット
uspto-grants-2016_03
特許番号
US09284335B2

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