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

HRID 1653738

반응식

HRID 1653738 반응식
[H-].[Na+].[C:3](=[N:7][OH:8])([NH2:6])[CH2:4][CH3:5].[C:9]1([C:15]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:16]2[CH2:21][CH:20]([C:22](OC)=O)[CH2:19][N:18]=[CH:17]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[C:32]1([C:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:16]2[CH2:21][CH:20]([C:22]3[O:8][N:7]=[C:3]([CH2:4][CH3:5])[N:6]=3)[CH2:19][N:18]=[CH:17]2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 4092053N-HydroxypropionimidamideHCID 100455711-Triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

생성물 1

HCID 100478851-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-ethyl-1,2,4-oxadiazol-5-yl)pyrimidine수율 71%

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 56 mg, 1.4 mmol) and propionamidoxime (123 mg, 1.4 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 (540 mg, 1.4 mmol) was added, dissolved in dry THF and reflux continued 18 hours. The solvents were evaporated in vacno and the residue was chromatographed (silica, chloroform/methanol 9:1) to yield 1-triphenylmethyl-1,4,5,6-tetrahydro-5-(3-ethyl-1,2,4-oxadiazol-5-yl)pyrimidine 420 mg (70%). This product was dissolved in trifluoroacetic 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 144 mg (49%) white crystals, mp 116°-118° 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 vacno
  8. customthe residue was chromatographed (silica, chloroform/methanol 9:1)

출처 및 근거

ORD 기록
ord-ef6d3d100e8f4c38a3fce3bf42375022
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05403845

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