Sodium hydride → 8-(2-methoxyethyl)-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2300075Notes

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.Br[CH2:22][CH2:23][O:24][CH3:25]>CN(C)C=O>[CH3:25][O:24][CH2:23][CH2:22][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]

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of NaH (49 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 (200 mg, 0.84 mmol). The reaction mixture was heated to 50° C. resulting in a yellow solution. The solution was cooled slightly, and 2-bromoethylmethyl ether (140 μL, 1.49 mmol) was added. The reaction mixture was heated at 50° C. for 10 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 a gradient of 2:1 hexane:ethyl acetate to all ethyl acetate gave 140 mg (56%) of 8-(2-methoxyethyl)-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one, mp 179-180° C.

Workup

customresulting in a yellow solution
temperatureThe solution was cooled slightly
temperatureThe reaction mixture was heated at 50° C. for 10 minutes
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 a gradient of 2:1 hexane

Sources & evidence

ORD record: ord-480047e5858a4d43b32c4c72043d322f
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498163B1

Reaction notes

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