5-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester → 5-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.2.1]octane-1-carboxylic acid

HRID 2105635ノート

反応式

HRID 2105635 の反応式
C([O:3][C:4]([C:6]12[CH2:13][C:10]([C:14](=O)[NH:15][C:16]3[C:17](=[O:30])[N:18]([CH2:27][CH2:28][CH3:29])[C:19](=[O:26])[N:20]([CH2:23][CH2:24][CH3:25])[C:21]=3[NH2:22])([CH2:11][CH2:12]1)[CH2:9][CH2:8][CH2:7]2)=[O:5])C>[OH-].[Na+].CO>[O:26]=[C:19]1[N:20]([CH2:23][CH2:24][CH3:25])[C:21]2[N:22]=[C:14]([C:10]34[CH2:13][C:6]([C:4]([OH:3])=[O:5])([CH2:12][CH2:11]3)[CH2:7][CH2:8][CH2:9]4)[NH:15][C:16]=2[C:17](=[O:30])[N:18]1[CH2:27][CH2:28][CH3:29]

参加物

4

反応物 1

HCID 670783425-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester

生成物 1

HCID 98432695-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo[3.2.1]octane-1-carboxylic acid収率 42.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

A solution of 5-(6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester (0.238 mmol, 0.10 g) in 20% NaOH (2.0 ml) and MeOH (10.0 ml) was stirred and refluxed 5 h. The reaction was cooled to room temperature and then concentrated to remove MeOH. The aqueous was acidified (pH 2-3) with conc. HCl and then extracted with EtOAc. The combined EtOAc extracts were washed with H2O and brine, and dried (MgSO4). Filtration and evaporation followed by reverse phase HPLC provided product (0.039 g, 42%) as a solid.

後処理

  1. temperaturerefluxed 5 h
  2. concentrationconcentrated
  3. customto remove MeOH
  4. extractionextracted with EtOAc
  5. washThe combined EtOAc extracts were washed with H2O and brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and evaporation

出典と根拠

ORDレコード
ord-4b9fc821cad549c4b9338fd4a4d8d7fb
出典データセット
uspto-grants-2009_08
特許番号
US07579354B2

反応ノート

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