(3-Hydroxymethyl-phenyl)-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-methanone → 3-[5-Isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidine-4-carbonyl]-benzaldehyde

HRID 426193노트

반응식

HRID 426193 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[C:16]([CH:17]([CH3:19])[CH3:18])=[C:15]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:14]=[C:13]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[N:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[CH:17]([C:16]1[C:11]([C:9]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[CH:2]=[O:1])=[O:10])=[N:12][C:13]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[N:14][C:15]=1[O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)([CH3:19])[CH3:18]

참가 물질

3

반응물 2

HCID 59184693(3-Hydroxymethyl-phenyl)-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-methanoneHCID 178418287HCID 178418287, 화합물

생성물 1

HCID 591848203-[5-Isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidine-4-carbonyl]-benzaldehyde수율 94.4%

실험 절차

A mixture of (3-hydroxymethyl-phenyl)-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-methanone (1.9 g, 3.52 mmol), pyridinium chlorochromate (1.14 g, 5.28 mmol), and dried celite (1 g) in dichloromethane (20 ml) was stirred for 1 hr. at room temperature. The mixture was then filtered through a short silica gel pad and the pad was washed with EA. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:4)) to afford 1.75 g (74%) of a pale yellow syrup. 1H NMR (200 MHz, CDCl3) δ 1.19 (6H, d, J=7.4 Hz), 2.88 (1H, m), 3.79 (3H, s), 3.83 (3H, s), 5.29 (2H, s), 5.45 (2H, s), 6.77-6.95 (4H, m), 7.28-7.42 (4H, m), 7.65 (1H, m), 8.11-8.28 (3H, m), 10.03 (1H, s).

후처리

  1. dry with materialdried celite (1 g) in dichloromethane (20 ml)
  2. customat room temperature
  3. filtrationThe mixture was then filtered through a short silica gel pad
  4. washthe pad was washed with EA
  5. customThe combined filtrate was evaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:4))

출처 및 근거

ORD 기록
ord-2850a8a07a604cad86c7281b89affbde
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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