Carbonic acid-guanidine (1:1) → tert-butyl 2-amino-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine-6-carboxylate

HRID 1052008Notes

Reaction equation

HRID 1052008 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[C:10](=[CH:15]N(C)C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)O.[NH2:23][C:24]([NH2:26])=[NH:25].O.O.O.C([O-])(=O)C.[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[N:25]=[C:24]([NH2:26])[N:23]=[CH:15][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 286947Carbonic acid-guanidine (1:1)HCID 23665404Sodium Acetate TrihydrateHCID 53395404tert-butyl 3-[(dimethylamino)methylene]-4-oxotetrahydro-1(2H)-pyridinecarboxylate

Product 1

HCID 29184118tert-butyl 2-amino-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine-6-carboxylateYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1-t-Butoxycarbonyl-3-(dimethylamino)methylene-4-piperidone (7.64 g, 30.04 mmol) in methanol (190 mL) was treated with guanidine carbonate (21.65 g, 120.16 mmol), followed by sodium acetate trihydrate (32.70 g, 240.32 mmol). The reaction mixture was heated at reflux for 17 hours and the solvent was removed in vacuo. The residue was diluted with water and the mixture was swirled for a few minutes. The undissolved white solid was collected and washed with water, followed by a small amount of cold ethyl acetate to give the title compound (4.10 g, 55%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 17 hours
  3. customthe solvent was removed in vacuo
  4. additionThe residue was diluted with water
  5. waitthe mixture was swirled for a few minutes
  6. customThe undissolved white solid was collected
  7. washwashed with water

Sources & evidence

ORD record
ord-69a4ce4bae804bdc81de4e1fb660c76b
Source dataset
uspto-grants-2016_07
Patent number
US09388176B2

Reaction notes

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