Ammonia → 6-(4-Fluorophenyl)pyrido[3,2-d]pyrimidin-4-amine

HRID 1517439Notes

Reaction equation

HRID 1517439 reaction equation
[NH3:1].Cl[C:3]1[C:4]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1>CO>[NH2:1][C:3]1[C:4]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[CH:10]=[CH:9][C:5]=2[N:6]=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 579067564-Chloro-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidine

Product 1

HCID 576983546-(4-Fluorophenyl)pyrido[3,2-d]pyrimidin-4-amineYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ammonia solution in methanol (5 ml of a 6 M solution) was added 4-chloro-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine (26 mg, 0.1 mmol). The mixture was stirred at room temperature for 12 hours. After concentration under reduced pressure, the residue was purified by silica gel flash chromatography, the mobile phase being a mixture of methanol and dichloromethane, in a volume ratio of 1:30, yielding the title compound (20 mg, yield 83%) as a white solid which was characterised by its mass spectrum as follows: MS (m/z): 241 ([M+H]+, 100).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was purified by silica gel flash chromatography
  3. additiona mixture of methanol and dichloromethane

Sources & evidence

ORD record
ord-c8c1b32e1e9649d1ae86b1ca3628fc0c
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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