1-Acetylpiperazine → Ethyl 2-(4-acetyl-1-piperazinyl)-5,8-dihydro-8-ethyl-5-oxopyrido[2,3-d]pyrimidine-6-carboxylate

HRID 1658114Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][C:5]2[C:11](=[O:12])[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][N:8]([CH2:18][CH3:19])[C:6]=2[N:7]=1.C(=O)(O)[O-].[Na+].[C:25]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)(=[O:27])[CH3:26]>CS(C)=O>[C:25]([N:28]1[CH2:33][CH2:32][N:31]([C:2]2[N:3]=[CH:4][C:5]3[C:11](=[O:12])[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][N:8]([CH2:18][CH3:19])[C:6]=3[N:7]=2)[CH2:30][CH2:29]1)(=[O:27])[CH3:26]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture containing 1.0 g of ethyl 2-chloro-5,8-dihydro-8-ethyl-5-oxopyrido[2,3-d]pyrimidine-6-carboxylate, 0.60 g of sodium bicarbonate, 20 ml of dimethyl sulfoxide, and 0.60 g of 1-acetylpiperazine was heated at 120°C for 1.5 hours with stirring. The dimethylsulfoxide was distilled off in vacuo and the residue was taken up in chloroform. The chloroform solution was washed with water, dried over anhydrous magnesium sulfate, and concentrated to dryness. The residual solid was recrystallized from a mixture of n-hexane and acetone to yield 1.21 of the product, m.p. 208°- 210°C with decomposition.

Workup

distillationThe dimethylsulfoxide was distilled off in vacuo
washThe chloroform solution was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated to dryness
customThe residual solid was recrystallized from a mixture of n-hexane and acetone
customto yield 1.21 of the product, m.p. 208°- 210°C with decomposition

Sources & evidence

ORD record: ord-3ae73c3b426b4aa3bb910352a0f60cc0
Source dataset: uspto-grants-1976_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03962443

Reaction notes

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