4-Amino-2-chlorophenol → 2-Chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenol

HRID 1864195Notes

Reaction equation

HRID 1864195 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[CH:4][N:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([Cl:21])[CH:15]=1.CC1C=C(NC2C3C(=CC=CC=3F)N=CN=2)C=CC=1O>>[Cl:21][C:16]1[CH:15]=[C:14]([NH:13][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][C:10]=3[F:12])[N:5]=[CH:4][N:3]=2)[CH:19]=[CH:18][C:17]=1[OH:20]

Participants

4

Reactant 3

HCID 775784-Amino-2-chlorophenolHCID 119744454-Chloro-5-fluoroquinazolineHCID 574449792-Methyl-4-[(5-fluoroquinazolin-4-yl)amino]phenol

Product 1

HCID 574449782-Chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenolYield 85%

Procedure

4-Chloro-5-fluoroquinazoline was reacted with 4-amino-2-chlorophenol using an analogous process to that described in Example 3 for the preparation of 2-methyl-4-[(5-fluoroquinazolin-4-yl)amino]phenol, to give 2-chloro-4-[(5-fluoroquinazolin-4-yl)amino]phenol in 85% yield; NMR spectrum (DMSO-d6) 6.97 (d, 1H), 7.38 (dd, 1H), 7.42 (dd, 1H), 7.59 (d, 1H), 7.73 (d, 1H), 7.81 (dd, 1H), 8.51 (s, 1H), 9.03 (d, 1H), 10.07 (bs, 1H); Mass spectrum MH+ 290.

Sources & evidence

ORD record
ord-f4328b262e244b95b7af9de2b346a154
Source dataset
uspto-grants-2009_12
Patent number
US07625908B2

Reaction notes

Loading…