Phosphorus oxychloride → N-(4,6-Dichloropyrido[3,2-d]pyrimidin-2-yl)acetamide

HRID 1517456Notes

Reaction equation

HRID 1517456 reaction equation
[C:1]([NH:4][C:5]1[NH:6][C:7](=O)[C:8]2[N:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:9]=2[N:10]=1)(=[O:3])[CH3:2].CCN(C(C)C)C(C)C.O=P(Cl)(Cl)[Cl:28]>O1CCOCC1>[Cl:28][C:7]1[C:8]2[N:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:9]=2[N:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[N:6]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 135978119N-(6-Chloro-4-oxo-1,4-dihydropyrido[3,2-d]pyrimidin-2-yl)acetamide

Product 1

HCID 57698319N-(4,6-Dichloropyrido[3,2-d]pyrimidin-2-yl)acetamideYield 78.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-acetamido-6-chloro-3H-pyrido[3,2-d]pyrimidin-4-one (2.38 g, 10 mmol) and DIEA (5.2 mL, 30 mmol) in dioxane (120 mL) was added POCl3 (2.8 mL, 30 mmol). The mixture was heated to 80° C. for 2 hours. After removal of solvent, the residue was stirred with crashed ice for 10 minutes, then extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to dryness providing the pure title compound as a brown solid (2.01 g, yield 78%) which was characterised as follows: MS (m/z) 256.9 [M+H]+.

Workup

  1. customAfter removal of solvent
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-13e4a5b4b4e94391ab8561517cdf9ee0
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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