2-Iodobutane → 8-sec-Butyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2300074Notes

Reaction equation

[H-].[Na+].[C:3]1([NH:9][C:10]2[N:11]=[CH:12][C:13]3[CH:19]=[CH:18][C:17](=[O:20])[NH:16][C:14]=3[N:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH:22]([CH2:24][CH3:25])[CH3:23]>CN(C)C=O>[CH:22]([N:16]1[C:14]2[N:15]=[C:10]([NH:9][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:11]=[CH:12][C:13]=2[CH:19]=[CH:18][C:17]1=[O:20])([CH2:24][CH3:25])[CH3:23]

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of NaH (47 mg of a 60% suspension of NaH in mineral oil) in 6 mL of dimethylformamide was added 2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one (202 mg, 0.85 mmol). The reaction mixture was heated to 50° C. to 60° C. resulting in a yellow solution. The solution was cooled slightly, and 2-iodobutane (140 μL, 1.22 mmol) was added. The reaction was heated at 50° C. for 20 minutes, then cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by flash chromatography eluting with 2:1 ethyl acetate:hexane gave 29 mg (12%) of 8-sec-butyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one, mp 155-156° C.

Workup

temperatureThe reaction mixture was heated to 50° C. to 60° C.
customresulting in a yellow solution
temperatureThe solution was cooled slightly
temperaturecooled to room temperature
custompartitioned between water and ethyl acetate
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by flash chromatography
washeluting with 2:1 ethyl acetate

Sources & evidence

ORD record: ord-f06ff9445277496eade8ac29d9c4c1cd
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498163B1

Reaction notes

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