4-[(5-{(1R)-2-[allyl(methyl)amino]-1-methylethoxy}quinazolin-4-yl)amino]-2-methylphenol → 2-methyl-4-({5-[(1R)-1-methyl-2-(methylamino) ethoxy]quinazolin-4-yl}amino)phenol
Reaction equation
[CH2:1]([N:4](C)[CH2:5][C@@H:6]([CH3:27])[O:7][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)C=C>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[CH3:26][C:21]1[CH:20]=[C:19]([NH:18][C:10]2[C:9]3[C:14](=[CH:15][CH:16]=[CH:17][C:8]=3[O:7][C@H:6]([CH3:27])[CH2:5][NH:4][CH3:1])[N:13]=[CH:12][N:11]=2)[CH:24]=[CH:23][C:22]=1[OH:25]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
The procedure described in Example 2.3 (preparation of starting materials) was repeated using chlorotris(triphenylphosphine)rhodium (I) and 4-[(5-{(1R)-2-[allyl(methyl)amino]-1-methylethoxy}quinazolin-4-yl)amino]-2-methylphenol to give 2-methyl-4-({5-[(1R)-1-methyl-2-(methylamino)ethoxy]quinazolin-4-yl}amino)-phenol as a brown foam in 56% yield; NMR spectrum (DMSO-d6) 1.41 (d, 3H), 2.15 (s, 3H), 2.33 (s, H), 2.87 (m, 2H), 4.85 (m, 1H), 6.77 (d, 1H), 7.14 (d, 1H), 7.25 (d, 1H), 7.43 (s, 1H), 7.46 (d, 1H), 7.64 (t, 1H), 8.38 (s, 1H), 9.14 (s, 1H), 10.35 (s, 1H); Mass spectrum MH+ 339.
Workup
- customThe procedure described in Example 2.3 (preparation of starting materials)
Sources & evidence
- ORD record
- ord-73fc9c23ae254ec49d62c8377db5b2d6
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625908B2
Reaction notes
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