Phenol → HCID 24879393, compound

HRID 16307Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([NH:19][C:20]2[CH:25]=[N:24][CH:23]=[C:22](Cl)[N:21]=2)[CH:12]=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16].[C:27]1([OH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[O:33]([C:22]1[N:21]=[C:20]([NH:19][C:11]2[CH:10]=[C:9]([O:8][CH3:7])[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=2)[CH:25]=[N:24][CH:23]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Reactant 3

HCID 996Phenol

HCID 11430Potassium Carbonate

HCID 116090492-(3,4,5-Trimethoxyphenylamino)-6-chloropyrazine

Product 1

HCID 24879393HCID 24879393, compoundYield 71%

Procedure

Using Method X (but with no addition of K2CO3) with 2-(3,4,5-trimethoxyphenylamino)-6-chloropyrazine (150 mg) and phenol, the title compound was obtained (127 mg). Yield: 71%. 1H NMR (250 MHz, DMSO-d6) δ 3.31 (s, 9H), 3.54 (s, 3H), 6.77 (s, 2H), 7.16-7.23 (m, 3H), 7.41 (t, 2H, J=7.9 Hz), 7.75 (s, 1H), 7.95 (s, 1H), 9.53 (s, 1H). 13C NMR (62.9 MHz, DMSO-d6) δ 55.33, 60.03, 95.77, 120.55, 121.17, 124.47, 128.42, 129.74, 132.15, 136.29, 150.52, 152.69, 153.86, 153.86, 157.23. m/z 354.1 [(M+H)+ calcd for C19H19N3O4 353.1].

Sources & evidence

ORD record: ord-d7611810d35c43b0a2ace09edaff581e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737152B2

Reaction notes

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