Sodium t-butoxide → HCID 178503401, 화합물

HRID 707262노트

반응식

HRID 707262 반응식
Cl[C:2]1[C:7]([C:8]([CH3:15])([CH3:14])[C:9]([O:11]CC)=O)=[CH:6][N:5]=[C:4]([S:16][CH3:17])[N:3]=1.[C:18]([O:22][C:23](=[O:30])[NH:24][C@H:25]1[CH2:28][C@H:27]([NH2:29])[CH2:26]1)([CH3:21])([CH3:20])[CH3:19].C1(P(C2CCCCC2)C2C(OC)=CC=C(OC)C=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC(C)([O-])C.[Na+]>O1CCOCC1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:18]([O:22][C:23](=[O:30])[NH:24][C@H:25]1[CH2:28][C@H:27]([N:29]2[C:2]3[N:3]=[C:4]([S:16][CH3:17])[N:5]=[CH:6][C:7]=3[C:8]([CH3:14])([CH3:15])[C:9]2=[O:11])[CH2:26]1)([CH3:21])([CH3:19])[CH3:20]

참가 물질

7

반응물 4

HCID 23676156Sodium t-butoxideHCID 25112535BrettphosHCID 86694234Ethyl 2-(4-chloro-2-(methylthio)pyrimidin-5-yl)-2-methylpropanoateHCID 178454111HCID 178454111, 화합물

생성물 1

HCID 178503401HCID 178503401, 화합물수율 31.4%

시약·촉매·용매 2

HCID 9832798Tris(dibenzylideneacetone) dipalladium촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A microwave vial containing a mixture of ethyl 2-(4-chloro-2-(methylthio)pyrimidin-5-yl)-2-methylpropanoate (2.08 g, 7.57 mmol), tert-butyl(trans-3-aminocyclobutyl)carbamate (1.551 g, 8.33 mmol), tris(dibenzylideneacetone) dipalladium (0) (0.520 g, 0.568 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.731 g, 1.363 mmol) and sodium tert-butoxide (2.317 ml, 18.93 mmol) in dioxane (15 mL) was purged with argon and capped. The reaction mixture was heated at 100° C. for 3 hours, cooled, and partitioned between water (200 mL) and ethyl actate (200 mL). The organic was isolated and concentrated under reduced pressure. Purification using the ISCO eluting with 0-70% EtOAc/hexane to give the desired product tert-butyl(trans-3-(5,5-dimethyl-2-(methylthio)-6-oxo-5H-pyrrolo[2,3-d]pyrimidin-7(6H)-yl)cyclobutyl)carbamate (0.9 g, 2.378 mmol, 31.4% yield). m/z: 379.2 (M+1).

후처리

  1. additionA microwave vial containing
  2. customwas purged with argon
  3. customcapped
  4. temperaturecooled
  5. custompartitioned between water (200 mL) and ethyl actate (200 mL)
  6. customThe organic was isolated
  7. concentrationconcentrated under reduced pressure
  8. customPurification
  9. washeluting with 0-70% EtOAc/hexane

출처 및 근거

ORD 기록
ord-8331d7a0352548eda94aba5b49ba6ad2
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174992B2

반응 노트

불러오는 중…