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

HRID 2175416Notes

Reaction equation

HRID 2175416 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-fc48a6758fe54b259a770e2ddbb9c16e
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

Loading…