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

HRID 426192노트

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HRID 426192 반응식
C([SiH2]OC(C)(C)C1C=C([CH:14]([C:17]2[C:22]([CH:23]([CH3:25])[CH3:24])=[C:21]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[N:20]=[C:19]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=3)[N:18]=2)C#N)C=CC=1)(C)(C)C.[H-].[Na+].[OH2:50].[C:51]1([CH3:61])[CH:56]=[CH:55][C:54](S(O)(=O)=O)=[CH:53][CH:52]=1.C[OH:63]>CN(C=O)C>[OH:50][CH2:61][C:51]1[CH:56]=[C:55]([C:14]([C:17]2[C:22]([CH:23]([CH3:24])[CH3:25])=[C:21]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=3)[N:20]=[C:19]([O:36][CH2:37][C:38]3[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=3)[N:18]=2)=[O:63])[CH:54]=[CH:53][CH:52]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 521998p-Toluenesulfonic acid monohydrateHCID 137328667[3-(tert-Butyl-dimethyl-silanyloxymethyl)-phenyl]-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-acetonitrile

생성물 1

HCID 59184693(3-Hydroxymethyl-phenyl)-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-methanone수율 40%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of [3-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-[5-isopropyl-2,6-bis-(4-methoxy-benzyloxy)-pyrimidin-4-yl]-acetonitrile (5.06 g, 7.75 mmol) in anhydrous DMF (30 ml), was added 60% sodium hydride (325 mg, 8.14 mmol). After 20 min., oxygen gas was bubbled into the reaction mixture for 3 hr. The mixture was partitioned between ether and aqueous saturated ammonium chloride solution. The ether layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was stirred with p-toluenesulfonic acid monohydrate (133 mg, 0.7 mmol) in methanol (10 ml) for 2 hr. at room temperature. The mixture was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:1 to 2:1)) to afford 1.67 g (40%) of a white foam. 1H NMR (200 MHz, CDCl3) δ 1.15 (6H, d, J=6.8 Hz), 1.96 (1H, t, J=5.6 Hz), 2.82 (1H, m), 3.78 (3H, s), 3.82 (3H, s), 4.70 (2H, d, J=5.6 Hz), 5.28 (2H, s), 5.42 (2H, s), 6.78-6.98 (4H, m), 7.30-7.52 (5H, m), 7.61-7.79 (3H, m).

후처리

  1. customoxygen gas was bubbled into the reaction mixture for 3 hr
  2. customThe mixture was partitioned between ether and aqueous saturated ammonium chloride solution
  3. washwashed with water twice
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customat room temperature
  8. customThe mixture was then evaporated in vacuo
  9. customthe residue was purified by silica gel column chromatography (eluent, ether: hexanes (from 1:1 to 2:1))

출처 및 근거

ORD 기록
ord-a5f236dcba2e45179162452fa3200700
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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