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

HRID 1592281

반응식

HRID 1592281 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 225997434-Chloro-6-(2-hydroxycyclohexyloxy)pyrimidine수율 34.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-983ef84057344271a3d6ba2331e3b870
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07291730B2

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