Iodoethane → 2-amino-6-(2,6-dichlorophenyl)-8-ethyl-7H,8H-pyrido[2,3-d]pyrimidin-7-one

HRID 3175

Reaction equation

[H-].[Na+].[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[C:11]([OH:22])=[N:10][C:8]=2[N:9]=1.[CH2:23](I)[CH3:24]>CN(C)C=O>[NH2:3][C:4]1[N:5]=[CH:6][C:7]2[CH:13]=[C:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:21])[C:11](=[O:22])[N:10]([CH2:23][CH3:24])[C:8]=2[N:9]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of NaH (60% in mineral oil, 27 mg) in 5 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (172 mg, 0.56 mmol) from Example 11. The mixture was heated at 50° C. for 1 hour resulting in a clear solution. Ethyl iodide (60 μL, 0.75 mmol) was added, and the solution was stirred at 50° C. for 3.5 hours, cooled to room temperature, and poured into 30 mL of ice water. The resulting precipitate was removed by filtration and partitioned between ethyl acetate and water. The organic layer was separated and dried over MgSO4, filtered, and concentrated in vacuo. Flash chromatography, eluting with ethyl acetate, provided 104 mg (55%) of 2-amino-6-(2,6-dichlorophenyl)-8-ethyl-pyrido[2,3-d]pyrimidin-7(8H)-one; mp 207°-209° C.

Workup

customresulting in a clear solution
temperaturecooled to room temperature
customThe resulting precipitate was removed by filtration
custompartitioned between ethyl acetate and water
customThe organic layer was separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
washFlash chromatography, eluting with ethyl acetate

Sources & evidence

ORD record: ord-dc089cf7000c4b12a70b5ffd130e6b36
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733914

Linked notes

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