Cesium carbonate → 2-(6-((1S,2S)-2-((6-chloro-2-methylpyrimidin-4-yloxy)methyl)cyclopropyl)pyridin-3-yl)propan-2-ol

HRID 2175416노트

반응식

HRID 2175416 반응식
[OH:1][CH2:2][C@H:3]1[CH2:5][C@@H:4]1[C:6]1[N:11]=[CH:10][C:9]([C:12]([OH:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=1.[Cl:16][C:17]1[CH:22]=[C:21](Cl)[N:20]=[C:19]([CH3:24])[N:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[Cl:16][C:17]1[N:18]=[C:19]([CH3:24])[N:20]=[C:21]([O:1][CH2:2][C@H:3]2[CH2:5][C@@H:4]2[C:6]2[N:11]=[CH:10][C:9]([C:12]([OH:15])([CH3:13])[CH3:14])=[CH:8][CH:7]=2)[CH:22]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 2349974,6-Dichloro-2-methylpyrimidineHCID 712743282-(6-((1S,2S)-2-(Hydroxymethyl)cyclopropyl)pyridin-3-yl)propan-2-ol

생성물 1

HCID 867295742-(6-((1S,2S)-2-((6-chloro-2-methylpyrimidin-4-yloxy)methyl)cyclopropyl)pyridin-3-yl)propan-2-ol수율 28%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of compound 8-2 (135 mg, 0.652 mmol) and 4,6-dichloro-2-methylpyrimidine (106.3 mg, 0.65 mmol) in THF (3.0 mL) was treated with Cs2CO3 (281 mg, 0.86 mmol) and heated to reflux for 12 h. The reaction mixture was filtrated and the filtrate was concentrated and purified directly by gradient elution on silica gel (Petroleum ether:ethyl acetate=2:1-1:1) to afford the title compound as a colorless oil (60 mg, 28%). LRMS (ES) calculated M+H for C17H20ClN3O2: 334.12. Found: 334.1.

후처리

  1. temperatureheated
  2. temperatureto reflux for 12 h
  3. filtrationThe reaction mixture was filtrated
  4. concentrationthe filtrate was concentrated
  5. custompurified directly by gradient elution on silica gel (Petroleum ether:ethyl acetate=2:1-1:1)

출처 및 근거

ORD 기록
ord-fc48a6758fe54b259a770e2ddbb9c16e
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062059B2

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