2-Methyl-4-[(5-fluoroquinazolin-4-yl)amino]phenol → 4-[(5-{(1R)-2-[allyl(methyl)amino]-1-methylethoxy}quinazolin-4-yl)amino]-2-methylphenol

HRID 1864312Notes

Reaction equation

HRID 1864312 reaction equation
[CH2:1]([N:4]([CH3:9])[CH2:5][C@H:6]([OH:8])[CH3:7])[CH:2]=[CH2:3].F[C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[C:13]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([CH3:29])[CH:23]=1)=[N:14][CH:15]=[N:16]2>>[CH2:1]([N:4]([CH3:9])[CH2:5][C@@H:6]([CH3:7])[O:8][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:12]=1[C:13]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([CH3:29])[CH:23]=1)=[N:14][CH:15]=[N:16]2)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 574449792-Methyl-4-[(5-fluoroquinazolin-4-yl)amino]phenolHCID 86615686(2R)-1-[allyl(methyl)amino]propan-2-ol

Product 1

HCID 690608864-[(5-{(1R)-2-[allyl(methyl)amino]-1-methylethoxy}quinazolin-4-yl)amino]-2-methylphenolYield 86%

Procedure

The procedure described in Example 3 (preparation of starting materials) was repeated using (2R)-1-[allyl(methyl)amino]propan-2-ol (obtained as described in Example 2.3, preparation of starting materials) and 4-[(5-fluoroquinazolin-4-yl)amino]-2-methylphenol (obtained as described in Example 3, preparation of starting materials) to give 4-[(5-{(1R)-2-[allyl(methyl)amino]-1-methylethoxy}quinazolin-4-yl)amino]-2-methylphenol as a brown oil in 86% yield; NMR spectrum (DMSO-d6) 1.43 (d, 3H), 2.15 (s, 3H), 2.18 (s, 3H), 2.54 (dd, 1H), 2.88 (dd, 1H), 3.00 (m, 2H), 4.92 (m, 1H), 5.01 (d, 1H), 5.11 (d, 1H), 5.62 (m, 1H), 6.77 (d, 1H), 7.16 (d, 1H), 7.26 (d, 1H), 7.35 (s, 1H), 7.38 (d, 1H), 7.66 (t, 1H), 8.37 (s, 1H), 9.17 (s, 1H), 10.16 (s, 1H); Mass spectrum MH+ 379.

Workup

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

Sources & evidence

ORD record
ord-1a75f449402c4ae1b7b7313f0b30b911
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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