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

HRID 1681907

반응식

HRID 1681907 반응식
[H-].[Na+].[C:3](=[N:8][OH:9])([NH2:7])[CH2:4][CH2:5][CH3:6].[C:10]1([C:16]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:17]2[CH2:22][CH:21]([C:23](OC)=O)[CH2:20][N:19]=[CH:18]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[C:33]1([C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:17]2[CH2:22][CH:21]([C:23]3[O:9][N:8]=[C:3]([CH2:4][CH2:5][CH3:6])[N:7]=3)[CH2:20][N:19]=[CH:18]2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 2794811N-HydroxybutyramidineHCID 100455711-Triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

생성물 1

HCID 103208401-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-n-propyl-1,2,4-oxadiazol-5-yl)pyrimidine수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

Prepared by a procedure similar to Example 9, where sodium hydride (60% dispersion in mineral oil 108 mg, 2.7 mmol) and butyramidoxime (276 mg, 2.7 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 (1.04 g, 2.7 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-propyl-1,2,4-oxadiazol-5-yl)pyrimidine 785 mg (67%). 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 240 mg (43%) white crystals, mp 126-128° C. identified by 300 MHz nmr.

후처리

  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)

출처 및 근거

ORD 기록
ord-29ab821c664d4f239d73b89ba7342a9b
출처 데이터셋
uspto-grants-1992_12
특허 번호
US05175166

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