2-acetamido-4-(N-isopropylamino)-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine → 2-amino-4-(N-isopropylamino)-6-(4-fluorophenyl)pyrido-[3,2-d]pyrimidine

HRID 1025520Notes

Reaction equation

HRID 1025520 reaction equation
C([NH:4][C:5]1[N:6]=[C:7]([NH:22][CH:23]([CH3:25])[CH3:24])[C:8]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=[CH:11][C:9]=2[N:10]=1)(=O)C>ClCCl.[O-]CC.[Na+]>[NH2:4][C:5]1[N:6]=[C:7]([NH:22][CH:23]([CH3:25])[CH3:24])[C:8]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=[CH:11][C:9]=2[N:10]=1

Participants

4

Reactant 1

HCID 690791042-acetamido-4-(N-isopropylamino)-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine

Product 1

HCID 690788992-amino-4-(N-isopropylamino)-6-(4-fluorophenyl)pyrido-[3,2-d]pyrimidineYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 2723922Sodium ethoxideSolvent

Procedure

The crude 2-acetamido-4-(N-isopropylamino)-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidine of example 3 (0.5 mmol) was suspended in a mixture of dichloromethane (10 ml) and 0.5 N sodium ethoxide (10 ml). The reaction mixture was stirred for 16 hours at room temperature. The solvents were evaporated in vacuo and the crude residue was purified by preparative thin layer chromatography on silica, using a mixture of methanol and dichloromethane (in a volume ratio of 10:90) as a mobile phase providing, in a yield of 61%, the pure title compound which was characterized by its mass spectra as follows: MS (m/z): 298 ([M+H]+, 100).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe crude residue was purified by preparative thin layer chromatography on silica
  3. additiona mixture of methanol and dichloromethane (in a volume ratio of 10:90) as a mobile phase
  4. customproviding, in a yield of 61%

Sources & evidence

ORD record
ord-40a2ec3b4a874195beecdd7ae42d7a90
Source dataset
uspto-grants-2014_05
Patent number
US08729089B2

Reaction notes

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