Ethyl 4-amino-1-piperidinecarboxylate → 3-(2-chlorophenyl)-7-(1-ethoxycarbonylpiperidin-4-ylamino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1280569Notes

Reaction equation

HRID 1280569 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13](S(CC3C=CC=CC=3)(=O)=O)=[N:14][CH:15]=2)[NH:10][C:9]1=[O:28].[NH2:29][CH:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:32][CH2:31]1>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([NH:29][CH:30]3[CH2:31][CH2:32][N:33]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:34][CH2:35]3)=[N:14][CH:15]=2)[NH:10][C:9]1=[O:28]

Participants

4

Reactant 2

HCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 180024743-(2-chlorophenyl)-7-benzylsulfonyl-3,4-dihydropyrimido[4,5-d]-pyrimidin-2(1H)-one

Product 1

HCID 184254663-(2-chlorophenyl)-7-(1-ethoxycarbonylpiperidin-4-ylamino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneYield 54.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

Sulfone 9.1 (1.0 g, 2.41 mmol) was taken up in 5 mL ethyl 4-amino-1-piperidinecarboxylate (29 mmol) and stirred at 150° C. After 1 hour, the reaction slurry was cooled to room temperature, poured into 50 mL methanol, and filtered to collect a white solid. The solid was washed with an additional 50 mL methanol and dried in vacuo to yield 0.569 g of 3-(2-chlorophenyl)-7-(1-ethoxycarbonylpiperidin-4-ylamino)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one.

Workup

  1. temperaturethe reaction slurry was cooled to room temperature
  2. filtrationfiltered
  3. customto collect a white solid
  4. washThe solid was washed with an additional 50 mL methanol
  5. customdried in vacuo

Sources & evidence

ORD record
ord-4c108898cb5b4869a3165063a290fdcf
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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