Phosphorus oxychloride → 4-Chloro-7-(cyclopropylmethoxy)pyrido[3,2-d]pyrimidine
Reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:15]=[N:14][C:13]3[C:12](=O)[N:11]=[CH:10][NH:9][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.C(N(C(C)C)CC)(C)C.P(Cl)(Cl)([Cl:28])=O>C1(C)C=CC=CC=1>[Cl:28][C:12]1[C:13]2[N:14]=[CH:15][C:6]([O:5][CH2:4][CH:1]3[CH2:3][CH2:2]3)=[CH:7][C:8]=2[N:9]=[CH:10][N:11]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
To a mixture of 7-(cyclopropylmethoxy)pyrido[3,2-d]pyrimidin-4(1H)-one (50 mg, 0.230 mmol) in Toluene (1.6 ml) were added diisopropylethylamine (122 μl, 0.702 mmol) and phosphorus oxychloride (65.3 μl, 0.714 mmol). The resulting reaction mixture was refluxed at 130° C. for 15 min. It was concentrated and the residue was dissolved in DCM and neutralized with sat. NaHCO3 until PH=6-7. The mixture was passed through silica plug. The filtrate was diluted with water and extracted with DCM for three times. The organic extract was washed with brine and dried over MgSO4. The solution was filtered and concentrated to give the crude material as a dark brown solid. It was used for next step directly. MS m/z=236.1 (M+H).
Workup
- customThe resulting reaction mixture
- concentrationIt was concentrated
- dissolutionthe residue was dissolved in DCM and neutralized with sat. NaHCO3 until PH=6-7
- additionThe filtrate was diluted with water
- extractionextracted with DCM for three times
- extractionThe organic extract
- washwas washed with brine
- dry with materialdried over MgSO4
- filtrationThe solution was filtered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c30c7845f22c4f6a837c1cbd4f91941a
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309263B2
Reaction notes
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