2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → 2-Methoxy-4-(6-{[(1S)-1-phenylethyl]amino}pyrazin-2-yl)phenol

HRID 1244390Notes

Reaction equation

HRID 1244390 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH:5]=[N:4][CH:3]=1.[CH3:17][O:18][C:19]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[CH:21][C:20]=1[OH:34]>>[CH3:17][O:18][C:19]1[CH:24]=[C:23]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([NH:8][C@H:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH3:10])[N:7]=2)[CH:22]=[CH:21][C:20]=1[OH:34]

Participants

3

Reactant 2

HCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 587170806-Chloro-N-[(1S)-1-phenylethyl]pyrazin-2-amine

Product 1

HCID 1354212422-Methoxy-4-(6-{[(1S)-1-phenylethyl]amino}pyrazin-2-yl)phenolYield 70%

Procedure

In a procedure analogous to Example 2, reaction of 6-chloro-N-[(1S)-1-phenylethyl]pyrazin-2-amine (717.3 mg, 3.07 mmol) and 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (845 mg, 3.38 mmol) furnished the product (689 mg, 70%).

Sources & evidence

ORD record
ord-ba6657afadab44d9a113ec8092cafdd8
Source dataset
uspto-grants-2006_10
Patent number
US07122550B2

Reaction notes

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