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

HRID 867179Notes

Reaction equation

HRID 867179 reaction equation
C1(OC2C=CC=CC=2)C=CC=CC=1.[C:14]([N:17]1[CH2:22][CH2:21][N:20]([C:23]2[N:28]=[C:27]([NH:29][CH:30]=[C:31]([C:37]([O:39]CC)=O)[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:26]=[CH:25][N:24]=2)[CH2:19][CH2:18]1)(=[O:16])[CH3:15]>CCCCCC>[C:14]([N:17]1[CH2:18][CH2:19][N:20]([C:23]2[N:24]=[CH:25][C:26]3[C:37](=[O:39])[C:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:30][NH:29][C:27]=3[N:28]=2)[CH2:21][CH2:22]1)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 13089622HCID 13089622, compound

Product 1

HCID 12917681Ethyl 2-(4-acetyl-1-piperazinyl)-5,8-dihydro-5-oxopyrido[2,3-d]pyrimidine-6-carboxylateYield 86.1%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To diphenyl ether (16ml) kept at 250°-255° C. was added with stirring diethyl N-[2-(4-acetyl-1-piperazinyl)-4-pyrimidinyl]-aminomethylenemalonate (2.0g). The mixture was gently refluxed for 10 minutes, and then allowed to cool to room temperature. To the mixture was added n-hexane (12ml). The resulting precipitate was collected, washed with ethanol, and recrystallized from ethanol to yield ethyl 2-(4-acetyl-1-piperazinyl)-5,8-dihydro-5-oxopyrido[2,3-d] pyrimidine-6-carboxylate (1.52 g), m.p. 300°-302° C. (decomp.).

Workup

  1. customkept at 250°-255° C.
  2. temperatureThe mixture was gently refluxed for 10 minutes
  3. customThe resulting precipitate was collected
  4. washwashed with ethanol
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-099ce91df6944038a729a6342d74f64a
Source dataset
uspto-grants-1978_07
Patent number
US04103011

Reaction notes

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