Hydrochloric Acid → HCID 178508882, compound

HRID 510230Notes

Reaction equation

HRID 510230 reaction equation
C(=O)(O)O.[NH2:5][C:6]([NH2:8])=[NH:7].Cl.[CH2:10]([N:17]1[CH2:22][CH2:21][CH:20]([C:23](OCC)=[O:24])[C:19](=O)[CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>CC(O)(C)C>[NH2:7][C:6]1[N:8]=[C:23]([OH:24])[C:20]2[CH2:21][CH2:22][N:17]([CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:18][C:19]=2[N:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 286947Carbonic acid-guanidine (1:1)HCID 2723880Ethyl 1-benzyl-3-oxopiperidine-4-carboxylate hydrochloride

Product 1

HCID 178508882HCID 178508882, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Guanidine carbonate (343 mg, 1.87 mmol) was added to a solution of 1-benzyl-4-ethoxycarbonyl-3-piperidone hydrochloride (488 mg, 1.87 mmol) in tBuOH (18 mL). The reaction was heated to reflux for 2 hours and then was acidified with 1N HCl to pH 5 and stirred for 30 minutes. The mixture was filtered and the solids were dried to obtain 2-amino-7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-ol as a yellow solid (320 mg, 67%). MS (ESI): mass calcd. for C14H16N4O 256.3 m/z found, 257.2[M+H]+. 1H NMR (500 MHz, MeOD) δ 7.40-7.26 (m, 5H), 3.71 (s, 2H), 3.25 (s, 2H), 2.73 (t, J=5.9 Hz, 2H), 2.46 (t, J=5.9 Hz, 2H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 hours
  3. filtrationThe mixture was filtered
  4. customthe solids were dried

Sources & evidence

ORD record
ord-c4bb94b9c77c4678ab75cab8bbb4bae3
Source dataset
uspto-grants-2015_08
Patent number
US09096596B2

Reaction notes

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