Ethyl Acetate → 4-(4-Hydroxy-phenylsulfanyl)-3-(7-isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-benzoic acid methyl ester

HRID 605350Notes

Reaction equation

[C:1]([C:3]1[C:4]([N:12]=[CH:13][N:14](C)C)=[N:5][C:6]([CH:9]([CH3:11])[CH3:10])=[CH:7][CH:8]=1)#[N:2].[CH3:17][O:18][C:19](=[O:35])[C:20]1[CH:25]=[CH:24][C:23]([S:26][C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[C:22](N)[CH:21]=1.CCOC(C)=O.C([O-])([O-])=O.[K+].[K+]>CC(O)=O.O>[CH3:17][O:18][C:19](=[O:35])[C:20]1[CH:21]=[CH:22][C:23]([S:26][C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)=[C:24]([NH:2][C:1]2[C:3]3[CH:8]=[CH:7][C:6]([CH:9]([CH3:10])[CH3:11])=[N:5][C:4]=3[N:12]=[CH:13][N:14]=2)[CH:25]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A suspension of N′-(3-cyano-6-isopropyl-pyridin-2-yl)-N,N-dimethyl-formamidine (0.75 g, 3.5 mmol) and 3-amino-4-(4-hydroxy-phenylsulfanyl)-benzoic acid methyl ester (0.96 g, 3.5 mmol) in AcOH (15 mL) was heated at 120° C. for 10 minutes under N2. The reaction mixture was portioned between AcOEt (10 mL) and H2O (150 mL) and made basic to pH 9 with K2CO3 under stirring. The resulting solid was collected by filtration, washed with H2O and AcOEt, and dried at 50° C. overnight under reduced pressure to give the title compound as pale brown crystal (1.27 g, 82%).

Workup

filtrationThe resulting solid was collected by filtration
washwashed with H2O and AcOEt
customdried at 50° C. overnight under reduced pressure

Sources & evidence

ORD record: ord-eabb3d2bd97c404399df16e6a7ee4877
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

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