Ethyl ethoxyacetate → 2-Butylsulfanyl-6-ethoxy-8,8a-dihydro-4ahpyrido[2,3-d]pyrimidin-7-one

HRID 459906

반응식

HRID 459906 반응식
[NH2:1][CH:2]1[CH:7]([CH:8]=O)[CH:6]=[N:5][C:4]([S:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N:3]1.[CH2:15]([O:17][CH2:18][C:19](OCC)=[O:20])[CH3:16].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[CH2:11]([S:10][C:4]1[N:5]=[CH:6][CH:7]2[CH:8]=[C:18]([O:17][CH2:15][CH3:16])[C:19](=[O:20])[NH:1][CH:2]2[N:3]=1)[CH2:12][CH2:13][CH3:14]

참가 물질

5

반응물 3

HCID 69955Ethyl ethoxyacetate2회HCID 21956055HCID 21956055, 화합물HCID 23665647Potassium tert-butoxide

생성물 1

HCID 219560512-Butylsulfanyl-6-ethoxy-8,8a-dihydro-4ahpyrido[2,3-d]pyrimidin-7-one

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

4-Amino-2-butylsulfanyl-4,5-dihydro-pyrimidine-5-carbaldehyde (3 g, 14.2 mmol, furnished by scaleup) and ethyl ethoxyacetate (2.34 g, 2.4 ml, 17.75 mmol) were stirred in 80 ml toluene at 0°-5° C. under nitrogen. Potassium t-butoxide (1.75 g, 15.6 mmol) was added gradually. The mixture was stirred to ambient temperature, and then to 65° C. for 48 hours. An additional 20 ml of toluene and 2.4 ml ethyl ethoxyacetate were added and the reaction was maintained at 65° C. over the weekend. The reaction mixture was concentrated in vacuo and triturated with EtOAc to remove the remaining starting aldehyde. The remaining solid was further triturated with chloroform to remove additional impurities. 3.66 g of 2-Butylsulfanyl-6-ethoxy-8,8a-dihydro-4aHpyrido[2,3-d]pyrimidin-7-one (1A) of a purity greater than 80% as judged by MS/HPLC and NMR was collected.

후처리

  1. temperaturethe reaction was maintained at 65° C. over the weekend
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customtriturated with EtOAc
  4. customto remove the remaining starting aldehyde
  5. customThe remaining solid was further triturated with chloroform
  6. customto remove additional impurities
  7. customwas collected

출처 및 근거

ORD 기록
ord-6cd10b64cb5b47d8a8a9f9930b4e7750
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196097B2

연결된 노트

불러오는 중…