Ethanolamine → 4-{[5-(2-Aminoethoxy)quinazolin-4-yl]amino}-2-methylphenol

HRID 1864295Notes

Reaction equation

HRID 1864295 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].F[C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH3:24])[CH:18]=1)=[N:9][CH:10]=[N:11]2>>[NH2:4][CH2:3][CH2:1][O:2][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH3:24])[CH:18]=1)=[N:9][CH:10]=[N:11]2

Participants

3

Reactant 2

HCID 700EthanolamineHCID 574449792-Methyl-4-[(5-fluoroquinazolin-4-yl)amino]phenol

Product 1

HCID 690591854-{[5-(2-Aminoethoxy)quinazolin-4-yl]amino}-2-methylphenolYield 23%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using ethanolamine and 4-[(5-fluoroquinazolin-4-yl)amino]-2-methylphenol (obtained as described in Example 3, preparation of starting materials) to give 4-{[5-(2-aminoethoxy)quinazolin-4-yl]amino}-2-methylphenol as a grey solid in 23% yield; NMR spectrum (DMSO-d6) 2.14 (s, 3H), 3.09 (d, 2H), 3.28 (s, 2H), 4.25 (t, 2H), 6.77 (d, 1H), 7.08 (d, 1H), 7.28 (d, 1H), 7.46 (dd, 1H), 7.55 (d, 1H), 7.66 (t, 1H), 8.40 (s, 1H), 10.31 (s, 1H); Mass spectrum MH+ 311.

Workup

  1. customThe procedure described in Example 3 (preparation of starting materials)

Sources & evidence

ORD record
ord-31960a7003bc49c3a1638f3c9bc96954
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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