1,4-Dioxane → 4-[(2RS,3SR)-(2,3,4-trihydroxybutan-1-yl)oxy]-2-(1-piperazinyl)quinazoline

HRID 1416503노트

반응식

HRID 1416503 반응식
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][CH2:28][CH:29]([OH:34])[CH:30]([OH:33])[CH2:31][OH:32])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.O1CCOCC1>CO.[Pd]>[OH:34][CH:29]([CH:30]([OH:33])[CH2:31][OH:32])[CH2:28][O:27][C:25]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([N:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)[N:26]=1

참가 물질

5

반응물 2

HCID 312751,4-DioxaneHCID 675828332-[4-(Benzyloxycarbonyl)piperazin-1-yl]-4-[(2,3,4-trihydroxybutan-1-yl)oxy]quinazoline

생성물 1

HCID 675821034-[(2RS,3SR)-(2,3,4-trihydroxybutan-1-yl)oxy]-2-(1-piperazinyl)quinazoline수율 55.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(2,3,4-trihydroxybutan-1-yl)oxy]quinazoline (800 mg) in methanol (6 ml)--dioxane (6 ml) is added 10% palladium/carbon (160 mg), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 17 hours. The reaction mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure. The residue is crystallized from acetone, and the resulting crystalline substance is recrystallized from ethanol-diethyl ether to give 4-[(2RS,3SR)-(2,3,4-trihydroxybutan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (316 mg) as crystals.

후처리

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness under reduced pressure
  3. customThe residue is crystallized from acetone
  4. customthe resulting crystalline substance is recrystallized from ethanol-diethyl ether

출처 및 근거

ORD 기록
ord-d3339fb909a7480da11b19d509def13c
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05912247

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