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Water → 4-{[(3R)-1-Benzylpiperidin-3-yl]oxy}-5-(4-ethylphenyl)-6-iodofuro[2,3-d]pyrimidine

HRID 2189072
ノート
印刷プレビュー

反応式

HRID 2189072 の反応式
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][C@@H:12]([OH:16])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:18]1[C:19]2[C:26]([C:27]3[CH:32]=[CH:31][C:30]([CH2:33][CH3:34])=[CH:29][CH:28]=3)=[C:25]([I:35])[O:24][C:20]=2[N:21]=[CH:22][N:23]=1.O>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][C@@H:12]([O:16][C:18]2[C:19]3[C:26]([C:27]4[CH:28]=[CH:29][C:30]([CH2:33][CH3:34])=[CH:31][CH:32]=4)=[C:25]([I:35])[O:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 693761(R)-(-)-1-Benzyl-3-hydroxypiperidineHCID 582802194-Chloro-5-(4-ethylphenyl)-6-iodofuro[2,3-d]pyrimidine

生成物 1

HCID 582800744-{[(3R)-1-Benzylpiperidin-3-yl]oxy}-5-(4-ethylphenyl)-6-iodofuro[2,3-d]pyrimidine

試薬・触媒・溶媒 3

HCID 67553
Tetrabutylammonium Iodide
触媒
HCID 8028Tetrahydrofuran溶媒2 回
HCID 8857Ethyl Acetate溶媒

実験手順

Add 106 mg (2.65 mmol) of sodium hydride (60% dispersion in mineral oil) to a solution of 483 mg (2.53 mmol) of (3R)-1-benzylpiperidin-3-ol [H. Tomori, Bull. Chem. Soc. Jpn. 69, 1, 207-216 (1996)] in 5 ml of THF. After stirring for ten minutes, add a solution of 1020 mg (70% purity, 1.86 mmol) of 4-chloro-5-(4-ethylphenyl)-6-iodofuro[2,3-d]pyrimidine in 5 ml of THF and 47 mg (0.13 mmol) of tetra-n-butylammonium iodide. Stir the reaction mixture at room temperature for five hours. After adding water and ethyl acetate, wash the removed organic phase with 1N hydrochloric acid and satd. sodium chloride solution and then concentrate under reduced pressure. Take up the residue in acetonitrile and purify by means of preparative RP-HPLC (gradient: water/acetonitrile). 266 mg (20% of theory) of the desired product are obtained.

後処理

  1. stirringStir the reaction mixture at room temperature for five hours
  2. washwash the removed organic phase with 1N hydrochloric acid
  3. concentrationsodium chloride solution and then concentrate under reduced pressure
  4. custompurify by means of preparative RP-HPLC (gradient: water/acetonitrile)

出典と根拠

ORDレコード
ord-051ca7fee2b24bc99674c09a67ef4dc0
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08324222B2

反応ノート

読み込み中…

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