Benzenamine, 4-(4-morpholinyl)- → C2 Pyrido[2,3-d]pyrimidin-7-one deriv. 34
Reaction equation
[CH2:1]([N:3]1[C:8]2[N:9]=[C:10](S(C)=O)[N:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]1=[O:16])[CH3:2].[O:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1>C(OCC)(=O)C>[CH2:1]([N:3]1[C:8]2[N:9]=[C:10]([NH:27][C:26]3[CH:25]=[CH:24][C:23]([N:20]4[CH2:21][CH2:22][O:17][CH2:18][CH2:19]4)=[CH:29][CH:28]=3)[N:11]=[CH:12][C:7]=2[CH:6]=[CH:5][C:4]1=[O:16])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 175 °C
Procedure
A mixture of 8-ethyl-2-methanesulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one (136 mg, 0.57 mmol) and 4-morpholinoaniline (205 mg, 1.15 mmol) was heated at 175° C. for 10 minutes then cooled to room temperature, and ethyl acetate was added. The precipitate was collected by filtration and purified by flash chromatography eluting with ethyl acetate. The fractions containing product were concentrated, and ethyl acetate and hexane were added to the residue. The resultant precipitate was collected by filtration to give 114 mg (57%) yield of 8-ethyl-2-(4-morpholin-4-yl-phenylamino)-8H-pyrido[2,3-d]pyrimidin-7-one, mp 227-228° C.
Workup
- temperaturethen cooled to room temperature
- filtrationThe precipitate was collected by filtration
- custompurified by flash chromatography
- washeluting with ethyl acetate
- additionThe fractions containing product
- concentrationwere concentrated
- additionethyl acetate and hexane were added to the residue
- filtrationThe resultant precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-2e9eb46c89e047d49df879852f90ffc4
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06498163B1
Reaction notes
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