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4-Chlorobenzyl alcohol → 6-(4-chlorobenzyloxy)-3-(4-(2-hydroxy-2-methyl-propoxy)-3-methoxyphenyl)pyrimidin-4(3H)-one

HRID 2059866
ノート
印刷プレビュー

反応式

HRID 2059866 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][CH:5]=1.Cl[C:13]1[N:18]=[CH:17][N:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]([OH:30])([CH3:29])[CH3:28])=[C:21]([O:31][CH3:32])[CH:20]=2)[C:15](=[O:33])[CH:14]=1>C1COCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:13]2[N:18]=[CH:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]([OH:30])([CH3:29])[CH3:28])=[C:21]([O:31][CH3:32])[CH:20]=3)[C:15](=[O:33])[CH:14]=2)=[CH:6][CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 133974-Chlorobenzyl alcoholHCID 24758Sodium hydrideHCID 585799166-chloro-3-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-pyrimidin-4(3H)-one

生成物 1

HCID 469267226-(4-chlorobenzyloxy)-3-(4-(2-hydroxy-2-methyl-propoxy)-3-methoxyphenyl)pyrimidin-4(3H)-one収率 5.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (13 mg, 0.32 mmol) was added to a solution of (4-chlorophenyl)methanol (46 mg, 0.32 mmol) in THF (1 mL) under nitrogen. The mixture was stirred at RT for 1 hour, then 6-chloro-3-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyrimidin-4(3H)-one Part A (35 mg, 0.108 mmol) was added and stirred for 45 min at RT. The reaction was quenched with MeOH (0.5 mL), diluted with EtOAc, washed with saturated NH4Cl, dried (Na2SO4), and concentrated. The residue was subjected to ISCO flash chromatography (silica gel/hexane-EtOAc 100:0 to 0:100 gradient). The product was then re-purified using HPLC (C18 column/10:90 to 90:10 MeOH—H2O) to afford the title compound 6-(4-chlorobenzyloxy)-3-(4-(2-hydroxy-2-methyl-propoxy)-3-methoxyphenyl)pyrimidin-4(3H)-one H-1 (2.5 mg, 5.2% yield). LC/MS 431 (M+H)+, tR 0.91 min (method 5); 1H NMR (400 MHz, chloroform-d) δ 6.04 (1H, s), 7.38 (4H, s), 7.00 (1H, d), 6.79-6.89 (2H, m), 5.85 (1H, s), 5.27 (2H, s), 3.87 (3H, s), 3.86 (2H, s), 1.36 (6H, s).

後処理

  1. stirringstirred for 45 min at RT
  2. customThe reaction was quenched with MeOH (0.5 mL)
  3. additiondiluted with EtOAc
  4. washwashed with saturated NH4Cl
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe product was then re-purified

出典と根拠

ORDレコード
ord-8486411d6fbb44d0bb669369d087cd7a
出典データセット
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08278316B2

反応ノート

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