Methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride → 6-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

HRID 583814Notes

Reaction equation

HRID 583814 reaction equation
[ClH:1].[CH2:2]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH:11]([C:16](OC)=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)(O)O.[NH2:24][C:25]([NH2:27])=[NH:26]>CCO>[CH2:2]([N:9]1[CH2:14][CH2:13][C:12]2[N:26]=[C:25]([NH2:27])[N:24]=[C:16]([Cl:1])[C:11]=2[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 107479Methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochlorideHCID 286947Carbonic acid-guanidine (1:1)

Product 1

HCID 143932216-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amineYield 131.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To EtOH (16 mL) cooled to 0° C. (ice/H2O bath) was added Na spheres (204 mg, 8.9 mmol). The mixture was stirred until all Na dissolved. Methyl 1-benzyl-4-oxo-3-piperidine-carboxylate hydrochloride (3.0 g, 10.1 mmol) and guanidine carbonate (1.4 g, 7.6 mmol) were added. The mixture was refluxed for 16 h. After the reaction was cooled to room temperature, the solid was collected by filtration, washed with EtOH, and dried under vacuum. Desired compound (2.58 g, 10.0 mmol; 99+% yield); mp=202-212° (dec.); ES MS [M+H]+=257; TLC (CH2Cl2—MeOH, 90:10); Rf=0.20. Step 2. Preparation of 6-benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine.

Workup

  1. additionwas added Na
  2. dissolutiondissolved
  3. temperatureThe mixture was refluxed for 16 h
  4. filtrationthe solid was collected by filtration
  5. washwashed with EtOH
  6. customdried under vacuum

Sources & evidence

ORD record
ord-8638429f722345ef8235b23fff3f6d60
Source dataset
uspto-grants-2005_08
Patent number
US06924290B2

Reaction notes

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