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

HRID 1244395Notes

Reaction equation

HRID 1244395 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH3:10])[CH:5]=[N:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=[CH:23][C:22]=1[OH:36]>>[CH3:19][O:20][C:21]1[CH:26]=[C:25]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([NH:8][C@H:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[CH3:10])[N:7]=2)[CH:24]=[CH:23][C:22]=1[OH:36]

Participants

3

Reactant 2

HCID 27346502-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 587170836-Chloro-N-[(1S)-1-(4-methoxyphenyl)ethyl]pyrazin-2-amine

Product 1

HCID 1361224392-Methoxy-4-(6-{[(1S)-1-(4-methoxyphenyl)ethyl]amino}pyrazin-2-yl)phenolYield 35.4%

Procedure

In a procedure analogous to Example 2, reaction of 6-chloro-N-[(15)-1-(4-methoxyphenyl)ethyl]pyrazin-2-amine (149.4 mg, 0.57 mmol) and 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (156 mg, 0.62 mmol) furnished the product (71 mg, 35%).

Sources & evidence

ORD record
ord-df9bac0a0ab54c74ab098f15904e6274
Source dataset
uspto-grants-2006_10
Patent number
US07122550B2

Reaction notes

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