Potassium Carbonate → 5-(4-[1,3]Dioxolan-2-yl-2-methylphenoxy)pyrazine-2-carbonitrile

HRID 492445

Reaction equation

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8](OC)[CH:7]=1.Cl[C:16]1[N:17]=[CH:18][C:19]([C:22]#[N:23])=[N:20][CH:21]=1.[C:24]([O-])([O-])=O.[K+].[K+]>CN(C=O)C.ClCCl>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:16]2[N:17]=[CH:18][C:19]([C:22]#[N:23])=[N:20][CH:21]=2)=[C:8]([CH3:24])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Take up 4-[1,3]dioxolan-2-yl-2-methylphenol (Example 388, Part C2) (0.288 g, 2.06 mmol), 5-chloropyrazine-2-carbonitrile (0.372 g, 2.06 mmol) and K2CO3 (0.428 g, 3.10 mmol) in DMF (13.8 mL). Beat at 100° C. for 45 minutes. Cool to 80° C. and stir overnight. Dilute the reaction mixture with dichloromethane (100 mL). Wash the organic layer with saturated aqueous NaHCO3 (2× 25 mL) and brine (1× 25 mL). Dry over Na2CO3, filter and concentrate. Purify by flash chromatography eluting with 30% ethyl acetate in hexanes to give the title compound (0.560 g, 95.58%): TLC [silica gel 60 F254, 30% ethyl acetate in hexanes] Rf=0.52.

Workup

washWash the organic layer with saturated aqueous NaHCO3 (2× 25 mL) and brine (1× 25 mL)
dry with materialDry over Na2CO3
filtrationfilter
concentrationconcentrate
customPurify by flash chromatography
washeluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-938ca2d1ab81497aba8f09eea58cccfd
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531557B2

Linked notes

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