(2R)-1-aminopropan-2-ol → 5-[(1R)-2-amino-1-methylethoxy]-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine

HRID 1864340Notes

Reaction equation

HRID 1864340 reaction equation
F[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:21]=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=3)=[C:15]([CH3:27])[CH:14]=1)=[N:5][CH:6]=[N:7]2.[NH2:28][CH2:29][C@H:30]([OH:32])[CH3:31]>>[NH2:28][CH2:29][C@@H:30]([CH3:31])[O:32][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:21]=[N:22][C:23]([CH3:26])=[CH:24][CH:25]=3)=[C:15]([CH3:27])[CH:14]=1)=[N:5][CH:6]=[N:7]2

Participants

3

Reactant 2

HCID 439938(2R)-1-aminopropan-2-olHCID 690241975-fluoro-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine

Product 1

HCID 690586035-[(1R)-2-amino-1-methylethoxy]-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amineYield 77%

Procedure

The procedure described in Example 103 (preparation of starting materials) was repeated using 5-fluoro-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine (obtained as described in Example 103, preparation of starting materials) and (2R)-1-aminopropan-2-ol to give 5-[(1R)-2-amino-1-methylethoxy]-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine in 77% yield; Mass spectrum: MH+ 416

Workup

  1. customThe procedure described in Example 103 (preparation of starting materials)

Sources & evidence

ORD record
ord-73a155092890495caed71a228a3cca3b
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

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