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

HRID 2175416ノート

反応式

HRID 2175416 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fc48a6758fe54b259a770e2ddbb9c16e
出典データセット
uspto-grants-2015_06
特許番号
US09062059B2

反応ノート

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