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

HRID 645510

반응식

HRID 645510 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f7943dc509964b26b286896b26da78a5
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07704996B2

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