Triethylamine → 2-Cyclobutyl-4-(dimethoxymethyl)pyrimidine

HRID 931110노트

반응식

HRID 931110 반응식
CN(C)[CH:3]=[CH:4][C:5](=O)[CH:6]([O:9][CH3:10])[O:7][CH3:8].Cl.[CH:14]1([C:18](=[NH:20])[NH2:19])[CH2:17][CH2:16][CH2:15]1.C(N(CC)CC)C>C(O)C>[CH:14]1([C:18]2[N:19]=[C:5]([CH:6]([O:9][CH3:10])[O:7][CH3:8])[CH:4]=[CH:3][N:20]=2)[CH2:17][CH2:16][CH2:15]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27821454-(Dimethylamino)-1,1-dimethoxybut-3-en-2-oneHCID 20542589Cyclobutanecarboximidamide--hydrogen chloride (1/1)

생성물 1

HCID 898540422-Cyclobutyl-4-(dimethoxymethyl)pyrimidine수율 12.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (2.0 g, 11.5 mmol) in ethanol was added cyclobutanecarboximidamide hydrochloride (3.0 g, 22.3 mmol) and triethylamine (2.33 g, 23.0 mmol) under nitrogen at room temperature. The reaction mixture was refluxed for 16 h. The solvent was removed under reduced pressure. To the residue was added water and the mixture was extracted with ethyl acetate. The combined organics were dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified via column chromatography to afford 2-cyclobutyl-4-(dimethoxymethyl)pyrimidine as a colorless liquid (300 mg, 12%). MS (ES+APCI) (M+H) 209.2; LCMS retention time: 3.257 minutes (Method J).

후처리

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. customThe solvent was removed under reduced pressure
  3. additionTo the residue was added water
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe combined organics were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified via column chromatography

출처 및 근거

ORD 기록
ord-b78243e5985c4b34b911760a8441cc87
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

반응 노트

불러오는 중…