Triphenylphosphine → 3-Butyl-8-chloro-1-[3-(1H-imidazol-4-yl)propyl]-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

HRID 1097638노트

반응식

HRID 1097638 반응식
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[N:10]([CH2:15][CH:16]=[CH2:17])[C:9]=2[C:8](=[O:18])[NH:7][C:6]1=[O:19])[CH2:2][CH2:3][CH3:4].[NH:20]1[CH:24]=[C:23]([CH2:25][CH2:26][CH2:27]O)[N:22]=[CH:21]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1>C1COCC1>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([Cl:14])[N:10]([CH2:15][CH:16]=[CH2:17])[C:9]=2[C:8](=[O:18])[N:7]([CH2:27][CH2:26][CH2:25][C:23]2[N:22]=[CH:21][NH:20][CH:24]=2)[C:6]1=[O:19])[CH2:2][CH2:3][CH3:4]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 592995823-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dioneHCID 178520509HCID 178520509, 화합물

생성물 1

HCID 1784563173-Butyl-8-chloro-1-[3-(1H-imidazol-4-yl)propyl]-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione수율 55.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 3-butyl-8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (2.8 g, 9.9 mmol) in anhydrous THF (60 ml) was treated with 3-(1H-imidazol-4-yl)-1-propanol (1.5 g, 12 mmol) in anhydrous THF (10 ml) and PPh3 (3.4 g, 13 mmol). DBAD (2.9 g, 13 mmol) was added in one portion and the mixture was left to stir at rt, under nitrogen for 18 h. The mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted and washed with EtOAc. The organic layers were combined, washed with brine, dried (MgSO4) and concentrated. The crude product was purified by a silica SPE cartridge using a MeOH/EtOAc gradient (0.5%-7% MeOH). The product fractions were combined and concentrated by to give the title compound as a white solid (2.16 g, 55%).

후처리

  1. waitthe mixture was left
  2. customThe mixture was partitioned between EtOAc and H2O
  3. extractionThe aqueous layer was extracted
  4. washwashed with EtOAc
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by a silica SPE cartridge
  9. concentrationconcentrated by

출처 및 근거

ORD 기록
ord-2a3edd7364c945a1a4a1a99e81fef3a8
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143264B2

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