Potassium Carbonate → HCID 21905995, compound

HRID 33448

Reaction equation

HRID 33448 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1)=O.C(=O)([O-])[O-].[K+].[K+].[C:25]([NH:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([NH2:35])=[O:34])=[CH:31][CH:30]=1)(=[NH:27])[NH2:26]>CCOCC>[C:33]([C:32]1[CH:36]=[CH:37][C:29]([NH:28][C:25]2[N:26]=[C:5]([C:7]3[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=3)[CH:4]=[CH:3][N:27]=2)=[CH:30][CH:31]=1)(=[O:34])[NH2:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21906035ethyl 4-[(2E)-3-(dimethylamino)prop-2-enoyl]benzoateHCID 178512510HCID 178512510, compound

Product 1

HCID 21905995HCID 21905995, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of ethyl 4-acetylbenzoate (3.00 g, 15.62 mmol) and N,N-dimethylformamide dimethyl acetal (6.2 g, 52.10 mmol) was refluxed for 18 hours, cooled and concentrated to give ethyl 4-[(2E)-3-(dimethylamino)prop-2-enoyl]benzoate quantitatively. A solution of ethyl 4-[(2E)-3-(dimethylamino)prop-2-enoyl]benzoate, potassium carbonate (3.55 g, 25.74 mmol), and 4-(amidinoamino)benzamide (3.10 g, 12.87 mmol) in ETOH (120 mL) was refluxed for 18 hours. The mixture was cooled, filtered, and washed with ETOH, water, then ether respectively to give ethyl 4-{2-[(4-carbamoylphenyl)amino]pyrimidin-4-yl}benzoate (2.60 g, 46% yield). This compound was refluxed for 2 hours in ETOH (30 mL), water (20 mL), and NaOH (0.640 g, 16 mmol). The reaction mixture was cooled, acidified to pH 3, and filtered to give 1.00 gram (42% yield) of the titled compound. HPLC/ES-MS (20-100% acetonitrile): R.T. 4.7 min.(Method A); (m/z) 335 [M+1]+.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washwashed with ETOH, water

Sources & evidence

ORD record
ord-97d811233f2d422a999e9b6c3caa486d
Source dataset
uspto-grants-2008_09
Patent number
US07429599B2

Linked notes

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