1,2-Cyclohexanediol → 4-Chloro-6-(2-hydroxycyclohexyloxy)pyrimidine

HRID 1592281ノート

反応式

HRID 1592281 の反応式
[H-].[Na+].[CH:3]1([OH:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[OH:9].[Cl:11][C:12]1[CH:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:11][C:12]1[CH:17]=[C:16]([O:9][CH:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH:3]2[OH:10])[N:15]=[CH:14][N:13]=1

参加物

6

反応物 4

HCID 136011,2-CyclohexanediolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

生成物 1

HCID 225997434-Chloro-6-(2-hydroxycyclohexyloxy)pyrimidine収率 34.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

In 30 ml of tetrahydrofuran was suspended 1.78 g of sodium hydride (60% in oil), to which 3 ml of a tetrahydrofuran solution containing 2.35 g of 1,2-cyclohexanediol (mixture of cis-form and trans-form) was slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 10 minutes and then cooled to 0° C., to which 7 ml of a tetrahydrofuran solution containing 3 g of 4,6-dichloropyrimidine was slowly added dropwise, followed by further stirring at 0° C. for 3 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with ethyl acetate. The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 1.6 g of 4-chloro-6-(2-hydroxycyclohexyloxy)pyrimidine.

後処理

  1. additionwas slowly added dropwise
  2. stirringThe mixture was stirred at room temperature for 10 minutes
  3. additionwas slowly added dropwise
  4. stirringby further stirring at 0° C. for 3 hours
  5. extractionextracted three times with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-983ef84057344271a3d6ba2331e3b870
出典データセット
uspto-grants-2007_11
特許番号
US07291730B2

反応ノート

読み込み中…