2,4-Dichloro-5-pyrimidinecarboxylic acid → 2-Chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid

HRID 645510

反応式

HRID 645510 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.CC([O-])(C)C.[K+].[CH2:18]1[C:20]2([CH2:25][CH2:24][CH:23]([CH2:26][OH:27])[CH2:22][CH2:21]2)[CH2:19]1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([O:27][CH2:26][CH:23]2[CH2:24][CH2:25][C:20]3([CH2:18][CH2:19]3)[CH2:21][CH2:22]2)[C:5]([C:9]([OH:11])=[O:10])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 219418962,4-Dichloro-5-pyrimidinecarboxylic acidHCID 23665647Potassium tert-butoxideHCID 53487089(Spiro(2.5)octan-6-yl)methanol

生成物 1

HCID 866277982-Chloro-4-(spiro[2.5]oct-6-ylmethoxy)pyrimidine-5-carboxylic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of a 2,4-dichloroprimidine-5-carboxylic acid (440 mg) in THF (4.0 mL) are added t-BuOK (potassium tert-butoxide) (5.7 mmol) and spiro[2.5]oct-6-ylmethanol (2.3 mmol) in THF (1.0 mL) at 0° C. After stirring at 0° C. for 1.5 h, the reaction is quenched by the addition of sat. aq. NaHCO3. The mixture is washed with ether. The aqueous layer is acidified to pH 2 with sat. aq. KHSO4, then extracted with AcOEt. The organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give the crude title compound.

後処理

  1. customthe reaction is quenched by the addition of sat. aq. NaHCO3
  2. washThe mixture is washed with ether
  3. extractionextracted with AcOEt
  4. washThe organic extracts are washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f7943dc509964b26b286896b26da78a5
出典データセット
uspto-grants-2010_04
特許番号
US07704996B2

関連ノート

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