Dimethylformamide dimethyl acetal → Ethyl 4-(4-cyanophenyl)-2-{[2-(2-quinolylamino)ethyl]amino}pyrimidine-5-carboxylate

HRID 1823416Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2].CN(C(OC)OC)C.[N:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[NH:35][CH2:36][CH2:37][NH:38][C:39]1[N:44]=C(C2C=CC(C(N)=O)=CC=2)C=[CH:41][N:40]=1.[O-]CC.[Na+]>C(O)C.C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:41][N:40]=[C:39]([NH:38][CH2:37][CH2:36][NH:35][C:26]3[CH:27]=[CH:28][C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:25]=3)[N:44]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 3-(4-cyanophenyl)3-oxopropanoate (64 mg, 0.3 mmol) was heated with DMFDMA (50 μl) and dry THF (1 ml) at 70° C. for 3 hours. The cooled mixture was then added to a suspension of amino[2-(2-quinolylamino)ethyl]carboxamidinium 4-methylbenzenesulfonate (prepared according to Example 12), (120 mg, 0.3 mmol) in ethanol (2 ml) containing 0.35 mmol of sodium ethoxide. The reaction was then heated at 80° C. overnight and then concentrated in vacuo. The residue was taken up in dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic layer was concentrated in vacuo. The residue was taken up in acetonitrile. Addition of water gave a precipitate which was filtered off and dried to give the title compound.

Workup

concentrationconcentrated in vacuo
washwashed with saturated aqueous sodium bicarbonate
concentrationThe organic layer was concentrated in vacuo
additionAddition of water
customgave a precipitate which
filtrationwas filtered off
customdried

Sources & evidence

ORD record: ord-fb51c0277fba47b89678dcf77088f186
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037918B2

Reaction notes

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