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

HRID 1653711

반응식

HRID 1653711 반응식
[H-].[Na+].[C:3](=[N:6][OH:7])([NH2:5])[CH3:4].[C:8]1([C:14]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:15]2[CH2:20][CH:19]([C:21](OC)=O)[CH2:18][N:17]=[CH:16]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[C:31]1([C:14]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:15]2[CH2:20][CH:19]([C:21]3[O:7][N:6]=[C:3]([CH3:4])[N:5]=3)[CH2:18][N:17]=[CH:16]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 30926N-HydroxyacetamidineHCID 100455711-Triphenylmethyl-5-methoxycarbonyl-1,4,5,6-tetrahydropyrimidine

생성물 1

HCID 100244281-Triphenylmethyl-1,4,5,6-tetrahydro-5-(3-methyl-1,2,4-oxadiazol-5-yl)pyrimidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

Sodium hydride (60% dispersion in mineral oil 26 mg, 0.65 mmol) and acetamidoxime (48 mg, 0.65 mmol) were suspended in dry THF (4 ml) 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 (250 mg, 0.65 mmol) was added dissolved in dry THF (3 ml) and reflux continued 18 hours. The solvents were evaporated in vacuo and the residue taken up in water (10 ml). The aqueous suspension was extracted exhaustively with chloroform and the organics dried over MgSO4. After evaporation the organic residue was chromatographed (silica, chloroform/methanol, 9:1) to yield 93 mg (rf=0.26, 35%) white crystals, mp 72°-74° C. identified by 300 MHz nmr and ms m/z=408. Calculated: C 76.44, H 5.9, N 13.7; found: C 76.27, H 6.06, N 13.59.

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. extractionThe aqueous suspension was extracted exhaustively with chloroform
  9. dry with materialthe organics dried over MgSO4
  10. customAfter evaporation the organic residue
  11. customwas chromatographed (silica, chloroform/methanol, 9:1)
  12. customto yield 93 mg (rf=0.26, 35%) white crystals, mp 72°-74° C.

출처 및 근거

ORD 기록
ord-baa858b8cc324c37b17b226965164d41
출처 데이터셋
uspto-grants-1995_04
특허 번호
US05403845

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