Pyridinium chloride → 4-[3-Chloro-4-fluoroanilino]-7-methoxyquinazolin-5-ol

HRID 1442981Notes

Reaction equation

Cl.N1C=CC=CC=1.[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH3:30])=[CH:24][C:25]=3[O:27]C)[N:20]=[CH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[F:15]>N1C=CC=CC=1.N.CO>[Cl:8][C:9]1[CH:10]=[C:11]([NH:16][C:17]2[C:26]3[C:25]([OH:27])=[CH:24][C:23]([O:29][CH3:30])=[CH:22][C:21]=3[N:20]=[CH:19][N:18]=2)[CH:12]=[CH:13][C:14]=1[F:15]

Participants

Conditions

Temperature: 115 °C

Procedure

Pyridine hydrochloride (2.33 g) was added in one portion to a stirred mixture of N-(3-chloro-4-fluorophenyl)-5,7-dimethoxyquinazolin-4-amine (6.4 g) in pyridine (75 ml) at room temperature. The reaction mixture was stirred at 115° C. under a nitrogen atmosphere for 23 hours and then the brown solution was cooled to room temperature and the yellow precipitate was filtered and washed with ice cold water to leave a light yellow solid. The solid was taken up in 7N ammonia in methanol and stirred at room temperature for 10 minutes. The solution was filtered and the filtrate was concentrated in vacuo to leave 4-[(3-chloro-4-fluorophenyl)-amino]-7-methoxyquinazolin-5-ol as a light brown solid (4.2 g, 68%); Mass spectrum MH+ 320.

Workup

temperaturethe brown solution was cooled to room temperature
filtrationthe yellow precipitate was filtered
washwashed with ice cold water
customto leave a light yellow solid
stirringstirred at room temperature for 10 minutes
filtrationThe solution was filtered
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-1c18b7f572c64c08a55386afa0ea393d
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659279B2

Reaction notes

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