Hydrochloric Acid → 3-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzaldehyde

HRID 426176ノート

反応式

HRID 426176 の反応式
C[O:2][CH:3](OC)[C:4]1[CH:5]=[C:6]([C:11]([C:13]2[C:18]([CH:19]([CH3:21])[CH3:20])=[C:17]([O:22][CH3:23])[N:16]=[C:15]([O:24][CH3:25])[N:14]=2)=[O:12])[CH:7]=[C:8]([CH3:10])[CH:9]=1.Cl>C(Cl)(Cl)Cl.CO>[CH:19]([C:18]1[C:13]([C:11]([C:6]2[CH:5]=[C:4]([CH:9]=[C:8]([CH3:10])[CH:7]=2)[CH:3]=[O:2])=[O:12])=[N:14][C:15]([O:24][CH3:25])=[N:16][C:17]=1[O:22][CH3:23])([CH3:21])[CH3:20]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 59184803(3-Dimethoxymethyl-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone

生成物 1

HCID 591848613-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-benzaldehyde収率 84%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6212Chloroform溶媒

実験手順

To a stirred solution of (3-dimethoxymethyl-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone (3.13 g, 8.36 mmol) in chloroform (30 ml) at room temperature, was added hydrogen chloride in methanol solution [prepared from methanol (30 ml) and acetyl chloride (4 ml)]. After stirring for 2 hr., the mixture was evaporated in vacuo. The residue was dissolved in ether, washed with aqueous saturated sodium bicarbonate solution, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, i) MC, ii) MC:EA (9:1)) to afford 2.3 g (84%) of a white solid. m.p. 111-113° C.; 1H NMR (300 MHz, CDCl3) δ 1.20 (6H, d, J=7.2 Hz), 2.50 (3H, s), 2.85 (1H, m), 3.93 (3H, s), 4.08 (3H, s), 7.94 (1H, s), 7.99 (1H, s), 8.08 (1H, s), 10.02 (1H, s).

後処理

  1. custom, the mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in ether
  3. washwashed with aqueous saturated sodium bicarbonate solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (eluent, i) MC, ii) MC

出典と根拠

ORDレコード
ord-4a73cc4c04c0445d875efba507738d51
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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