Water → 7-[2-(3-Fluoro-pyridin-2-YL)-imidazol-1-ylmethyl]-2-isopropoxy-8-propyl-[1,2,4]-triazolo[1,5-C]pyrimidine

HRID 916670Notes

Reaction equation

[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]4[N:20]=[C:21]([OH:23])[N:22]=[C:16]4[C:15]=3[CH2:24][CH2:25][CH3:26])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].I[CH:34]([CH3:36])[CH3:35].O>CN(C=O)C>[F:1][C:2]1[C:3]([C:8]2[N:9]([CH2:13][C:14]3[N:19]=[CH:18][N:17]4[N:20]=[C:21]([O:23][CH:34]([CH3:36])[CH3:35])[N:22]=[C:16]4[C:15]=3[CH2:24][CH2:25][CH3:26])[CH:10]=[CH:11][N:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To the solution of compound 177 in DMF (10 mL) is added anhydrous potassium carbonate (2 eq.) and 2-iodopropane (2 eq.). The resulting mixture is stirred at 60° C. overnight. On cooling the reaction mixture is poured into water (50 mL) and the mixture extracted with dichloromethane, dried over sodium sulfate. The organic solution is concentrated and purified with PTLC to give product 176 as sticky oil. LCMS (M+1) 396.3.

Workup

temperatureOn cooling the reaction mixture
extractionthe mixture extracted with dichloromethane
dry with materialdried over sodium sulfate
concentrationThe organic solution is concentrated
custompurified with PTLC

Sources & evidence

ORD record: ord-20037ee3d6db4505b825e0508561ef73
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271170B2

Reaction notes

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