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

HRID 426192ノート

反応式

HRID 426192 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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))

出典と根拠

ORDレコード
ord-a5f236dcba2e45179162452fa3200700
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

反応ノート

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