Sodium Acetate → HCID 86671078, compound

HRID 1485536Notes

Reaction equation

HRID 1485536 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][N:8]=[C:9](OC3CCOCC3)[C:10]=2[N:11]=1.[F:19][C:20]([F:30])([F:29])[O:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1.C([O-])(=O)C.[Na+]>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:26][C:25]3[CH:27]=[CH:28][C:22]([O:21][C:20]([F:19])([F:29])[F:30])=[CH:23][CH:24]=3)[C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 6008484-(Trifluoromethoxy)anilineHCID 866710656-chloro-4-[(tetrahydro-2H-pyran-4-yl)oxy]-Pyrido[3,2-d]pyrimidine2×

Product 1

HCID 86671078HCID 86671078, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4,6-dichloropyrido[3,2-d]pyrimidine (Intermediate 1, step D) (0.200 g, 1.00 mmol), 4-(trifluoromethoxy)aniline (0.177 g, 1.00 mmol) and sodium acetate (0.246 g, 3.00 mmol) in 5 ml of solvent (THF:H2O=1:1) was refluxed for 1 hour. The reaction mixture was diluted with EtOAc. The organics were washed with brine, dried over Na2SO4, filtered and concentrated. The crued was purified by column chromatography on SiO2 (Hex:EtOAc=1:1) to get 6-chloro-N-(4-(trifluoromethoxy)phenyl)pyrido[3,2-d]pyrimidin-4-amine (0.32 g, 94%) as a yellow solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 7.30 (1H, d, J=8.4 Hz), 7.72 (1H, d, J=8.8 Hz), 7.98 (1H, d, J=9.2 Hz), 8.15 (1H, dd, J=8.8 Hz), 8.80 (1H, s), 8.90 (1H, br s).

Workup

  1. temperaturewas refluxed for 1 hour
  2. washThe organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crued was purified by column chromatography on SiO2 (Hex:EtOAc=1:1)

Sources & evidence

ORD record
ord-d0b5dff543f64657b371d4a7424a52a5
Source dataset
uspto-grants-2016_08
Patent number
US09422298B2

Reaction notes

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