Hydrochloric Acid → 3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}butan-2-ol

HRID 1926913ノート

反応式

HRID 1926913 の反応式
[OH-].[Na+].[CH3:3][C@@H:4]([OH:8])[C@@H:5]([OH:7])[CH3:6].Cl[C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1.Cl>C1(C)C=CC=CC=1.COCCOC.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]2[C:11]3[C:10]([O:7][CH:5]([CH3:6])[CH:4]([OH:8])[CH3:3])=[N:15][CH:14]=[N:13][C:12]=3[O:16][C:17]=2[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:24][CH:23]=1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 220010Meso-2,3-ButanediolHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

生成物 1

HCID 580169433-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}butan-2-ol

試薬・触媒・溶媒 4

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
70 °C

実験手順

Add 4.8 ml of 12.5 N sodium hydroxide solution to a mixture of 2.68 g (29.70 mmol) (2R,3S)-butane-2,3-diol in 45 ml toluene, 15 ml 1,2-dimethoxyethane and 15 ml water at 70° C. After adding 0.20 g (0.60 mmol) tetra-n-butylammonium hydrogensulphate and 2.00 g (5.94 mmol) 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine, stir the reaction mixture for 17 h at 70° C. After cooling to room temperature, adjust to pH 7 with concentrated hydrochloric acid. Extract three times with 100 ml dichloromethane each time. Wash the combined organic extracts with satd. sodium chloride solution, dry over sodium sulphate, filter, and concentrate by vacuum evaporation. Purify the raw product by preparative RP-HPLC (gradient: water/acetonitrile). 1.26 g (54% of theor.) of the desired product is obtained as (R,S/S,R) racemate.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionExtract three times with 100 ml dichloromethane each time
  3. washWash the combined organic extracts with satd
  4. dry with materialsodium chloride solution, dry over sodium sulphate
  5. filtrationfilter
  6. concentrationconcentrate by vacuum evaporation
  7. customPurify the raw product by preparative RP-HPLC (gradient: water/acetonitrile)

出典と根拠

ORDレコード
ord-32d0a414306343448d7dd9c2334e1938
出典データセット
uspto-grants-2012_05
特許番号
US08183246B2

反応ノート

読み込み中…