Sodium hydride → 1-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-n-pentyl-1,2,4-oxadiazol-5-yl)pyrimidine

HRID 1681908

反応式

HRID 1681908 の反応式
[H-].[Na+].[C:3](=[N:10][OH:11])([NH2:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:12]1([C:18]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:19]2[CH2:24][CH:23]([C:25](OC)=O)[CH2:22][N:21]=[CH:20]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[C:35]1([C:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:19]2[CH2:24][CH:23]([C:25]3[O:11][N:10]=[C:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[N:9]=3)[CH2:22][N:21]=[CH:20]2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 3613628N'-hydroxyhexanimidamideHCID 100455711-Triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

生成物 1

HCID 103443951-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-n-pentyl-1,2,4-oxadiazol-5-yl)pyrimidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Prepared by a procedure similar to Example 9, where sodium hydride (95% 40 mg, 1.7 mmol) and n-hexanamidoxime (217 mg, 1.7 mmol) were suspended in dry THF in an oven dried round bottom flask with stirring under nitrogen at 0° C. After 15 minutes stirring the ice bath was removed and the grey suspension refluxed 45 minutes to give a white suspension. 1-Triphenylmethyl-1,4,5,6-tetrahydro-5-methoxycarbonylpyrimidine (640 mg, 1.7 mmol) was added, dissolved in dry THF and reflux continued 18 hours. The solvents were evaporated in vacuo and the residue was chromatographed (silica, chloroform/methanol, 9:1) to yield 1-triphenylmethyl-1,4,5,6-tetrahydro-5-(3-n-pentyl-1,2,4-oxadiazol-5-yl)pyrimidine. This product was dissolved in triflouroacetic acid (2 mL), with stirring at room temperature for 24 hours. The yellow solution was then evaporated in vacuo, and the residue recrystallized from methanol/ether to yield 110 mg (19%) white crystals, mp 97°-99° C. identified by 300 MHz nmr.

後処理

  1. customdried round bottom flask
  2. stirringAfter 15 minutes stirring the ice bath
  3. customwas removed
  4. temperaturethe grey suspension refluxed 45 minutes
  5. customto give a white suspension
  6. temperaturereflux
  7. customThe solvents were evaporated in vacuo
  8. customthe residue was chromatographed (silica, chloroform/methanol, 9:1)

出典と根拠

ORDレコード
ord-37ac5ad644f144b185c660d9b3be21bc
出典データセット
uspto-grants-1992_12
特許番号
US05175166

関連ノート

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