Carbonic acid-guanidine (1:1) → 2-Amino-5,6,7,8-tetrahydro-6-triphenylmethylpyrido-[4,3-d]pyrimidine

HRID 2247942Notes

Reaction equation

HRID 2247942 reaction equation
CN(C=[C:5]1[CH2:10][C:9](=O)[CH2:8][CH2:7][N:6]1[C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C.[C:31](=O)(O)O.[NH2:35][C:36]([NH2:38])=[NH:37]>C(OCC)(=O)C>[NH2:37][C:36]1[N:38]=[CH:31][C:8]2[CH2:7][N:6]([C:12]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:5][CH2:10][C:9]=2[N:35]=1

Participants

4

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 570413702-[(Dimethylamino)methylene]-1-triphenylmethyl-4-piperidone

Product 1

HCID 150176612-Amino-5,6,7,8-tetrahydro-6-triphenylmethylpyrido-[4,3-d]pyrimidineYield 80.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-[(Dimethylamino)methylene]-1-triphenylmethyl-4-piperidone (0.172 g, 0.434 mmol) was dissolved in ethyl acetate (4 ml) and treated with guanidine carbonate (47 mg, 0.260 mmol). The reaction mixture was heated to reflux for sixteen hours, and then concentrated in vacuo. Purification of the residue via flash column chromatography (eluant: 3:1 ethyl acetate: hexanes) yielded the title product as a yellow oil (83 mg, 0.21 mmol, 48% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for sixteen hours
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue via flash column chromatography (eluant: 3:1 ethyl acetate: hexanes)

Sources & evidence

ORD record
ord-9a51120944b945d0ac576419f3366ec5
Source dataset
uspto-grants-1991_08
Patent number
US05037834

Reaction notes

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