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

HRID 1760003ノート

反応式

HRID 1760003 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-a53272c4b1f742e183ffb70e16279917
出典データセット
uspto-grants-2005_01
特許番号
US06838463B2

反応ノート

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