Methanol → N-(3-chloro-4-fluorophenyl)-5,7-dimethoxyquinazolin-4-amine

HRID 1442980Notes

Reaction equation

HRID 1442980 reaction equation
[CH3:1][OH:2].C[C:4](C)([O-:6])C.[K+].[Cl:9][C:10]1[CH:11]=[C:12]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24](F)=[CH:25][C:26]=3F)[N:21]=[CH:20][N:19]=2)[CH:13]=[CH:14][C:15]=1[F:16].O>C1COCC1>[Cl:9][C:10]1[CH:11]=[C:12]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:6][CH3:4])=[CH:25][C:26]=3[O:2][CH3:1])[N:21]=[CH:20][N:19]=2)[CH:13]=[CH:14][C:15]=1[F:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 68676704N-(3-chloro-4-fluorophenyl)-5,7-difluoroquinazolin-4-amine

Product 1

HCID 68675529N-(3-chloro-4-fluorophenyl)-5,7-dimethoxyquinazolin-4-amineYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

Methanol (6.5 ml) and potassium tert-butoxide (18 g) were added sequentially, each in one portion, to a mixture of N-(3-chloro-4-fluorophenyl)-5,7-difluoroquinazolin-4-amine (13.8 g) in THF (270 ml) at room temperature under a nitrogen atmosphere. The mixture was heated at 75° C. for 18 hours 30 minutes and then cooled to room temperature and concentrated in vacuo to leave a brown solid. The solid was cooled to 0° C. and cold water was added and then the precipitate was filtered and dried to leave N-(3-chloro-4-fluorophenyl)-5,7-dimethoxyquinazolin-4-amine as a light brown solid (10.4 g, 69%); Mass spectrum MH+ 334.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto leave a brown solid
  4. temperatureThe solid was cooled to 0° C.
  5. filtrationthe precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-e49ab3aeb59a44fc87b6ea50dee6105d
Source dataset
uspto-grants-2010_02
Patent number
US07659279B2

Reaction notes

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