2,6-Lutidine → 4-Chloro-6-(3,4-dimethoxyphenyl)pyrido[3,2-d]pyrimidine

HRID 1517390Notes

Reaction equation

HRID 1517390 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[CH:13][C:14]3[N:15]=[CH:16][NH:17][C:18](=O)[C:19]=3[N:20]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Cl)(Cl)([Cl:24])=O.N1C(C)=CC=CC=1C>C1(C)C=CC=CC=1>[Cl:24][C:18]1[C:19]2[N:20]=[C:11]([C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:12]=[CH:13][C:14]=2[N:15]=[CH:16][N:17]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 1362700206-(3,4-Dimethoxyphenyl)pyrido[3,2-d]pyrimidin-4(1H)-one

Product 1

HCID 714077034-Chloro-6-(3,4-dimethoxyphenyl)pyrido[3,2-d]pyrimidineYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 6-(3,4-dimethoxyphenyl)-pyrido[3,2-d]pyrimidin-4(3H)-one (150 mg, 0.53 mmol) in toluene (30 ml) was added phosphorus oxychloride (148 μl, 1.59 mmol) and 2,6-lutidine (185 μl, 1.59 mmol). The reaction mixture was refluxed overnight until a black solution was obtained. After evaporation to dryness, the residue was redissolved in ethyl acetate and extracted with a saturated sodium bicarbonate solution. The combined organic layers were evaporated in vacuo. The residue was purified by silica gel column chromatography, the mobile phase being an ethyl acetate/hexane mixture, in a ratio gradually ranging from 2:8 to 3:7, resulting in the pure title compound (123 mg, yield 77%) which was characterised by its mass spectrum as follows: MS (m/z): 302, 304 ([M+H]+, 100).

Workup

  1. temperatureThe reaction mixture was refluxed overnight until a black solution
  2. customwas obtained
  3. customAfter evaporation to dryness
  4. dissolutionthe residue was redissolved in ethyl acetate
  5. extractionextracted with a saturated sodium bicarbonate solution
  6. customThe combined organic layers were evaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0fe63467e924417d8b5f2108e5f24f04
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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