2-Amino-2-methyl-1-propanol → 4-{[5-(2-Amino-2-methylpropoxy)quinazolin-4-yl]amino}-2-methylphenol

HRID 1864298Notes

Reaction equation

HRID 1864298 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].F[C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[C:10]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH3:26])[CH:20]=1)=[N:11][CH:12]=[N:13]2>>[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][O:4][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[C:10]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([CH3:26])[CH:20]=1)=[N:11][CH:12]=[N:13]2

Participants

3

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 574449792-Methyl-4-[(5-fluoroquinazolin-4-yl)amino]phenol

Product 1

HCID 690609524-{[5-(2-Amino-2-methylpropoxy)quinazolin-4-yl]amino}-2-methylphenolYield 78%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using 2-amino-2-methylpropan-1-ol and 4-[(5-fluoroquinazolin-4-yl)amino]-2-methylphenol (obtained as described in Example 3, preparation of starting materials) to give 4-{[5-(2-amino-2-methylpropoxy)quinazolin-4-yl]amino}-2-methylphenol as a white solid in 78% yield; NMR spectrum (DMSO-d6) 1.34 (s, 6H), 4.23 (s, 2H), 6.97 (d, 1H), 7.18 (d, 1H), 7.35 (d, 1H), 7.52 (dd, 1H), 7.73 (t, 1H), 7.96 (d, 1H), 8.46 (s, 1H), 10.50 (s, 1H); Mass spectrum MH+ 360.

Workup

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

Sources & evidence

ORD record
ord-d480f408891842e1aba02fb2817386d7
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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