Pyridine → 2-(4-(2-Hydroxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acid

HRID 1399688ノート

反応式

HRID 1399688 の反応式
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([O:18]C)=[O:17])=[C:13]([CH3:23])[N:12]=[C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:10]=1.[I-].[Li+].N1C=CC=C[CH:33]=1>>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([OH:18])=[O:17])=[C:13]([CH3:23])[N:12]=[C:11]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:10]=1.[CH3:33][O:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([OH:18])=[O:17])=[C:13]([CH3:23])[N:12]=[C:11]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:10]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 66321Lithium iodideHCID 136126955Methyl 2-(4-(2-hydroxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate

生成物 2

HCID 509975072-(4-(2-Methoxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acid収率 5%HCID 1361269632-(4-(2-Hydroxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acid収率 21%

実験手順

A solution of methyl 2-(4-(2-hydroxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.040 g; 0.099 mmol) and lithium iodide (0.066 g; 0.494 mmol) in pyridine (0.5 mL) was irradiated at 170° C. in a microwave sealed tube for 3 h. The solvent was removed under reduced pressure, the residue was dissolved in water and the pH adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N. The suspension was extracted twice with ethyl acetate and the combined organic layers were concentrated under reduced pressure. The residue was again suspended in water, basified with a solution of sodium hydroxide 5N and washed with a mixture of heptane and ethyl acetate (1:1). The pH of the aqueous solution was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N, extracted twice with ethyl acetate and the combined organic layers were dried over magnesium sulphate and concentrated under reduced pressure. Purification by preparative HPLC (HPLC method 1) furnished 0.008 g (21%) of 2-(4-(2-hydroxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acid and 0.002 g (5%) of 2-(4-(2-methoxy-4-methylphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoic acid.

後処理

  1. customsealed tube for 3 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. additionthe pH adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N
  5. extractionThe suspension was extracted twice with ethyl acetate
  6. concentrationthe combined organic layers were concentrated under reduced pressure
  7. washwashed with a mixture of heptane and ethyl acetate (1:1)
  8. additionThe pH of the aqueous solution was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N
  9. extractionextracted twice with ethyl acetate
  10. dry with materialthe combined organic layers were dried over magnesium sulphate
  11. concentrationconcentrated under reduced pressure
  12. customPurification by preparative HPLC (HPLC method 1)

出典と根拠

ORDレコード
ord-ddff29327c9b4afd911f468aeffea416
出典データセット
uspto-grants-2014_12
特許番号
US08906906B2

反応ノート

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