Guanidine Hydrochloride → tert-butyl 2-amino-5H,6H,7H,8H-pyrido[4,3-d]pyrimidine-6-carboxylate

HRID 1444592Notes

Reaction equation

HRID 1444592 reaction equation
Cl.[NH2:2][C:3]([NH2:5])=[NH:4].[Na].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17](=O)[C:16](=[CH:21]N(C)C)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>C(O)C>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]2[N:4]=[C:3]([NH2:5])[N:2]=[CH:21][C:16]=2[CH2:15]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 5742Guanidine HydrochlorideHCID 5360545SodiumHCID 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 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Guanidine hydrochloride 7.07 g (74 mmol) was added at 0° C. to a solution of sodium 1.65 g (74 mmol) in absolute ethanol and stirring was performed for 2 h at RT under nitrogen as inert gas. 60 ml (60 mmol) of this reaction mixture were added to the solution of 3-dimethylaminomethylene-4-oxo-piperidine-1-carboxylic acid tert-butyl ester in 100 ml of absolute ethanol and refluxing was performed for 5 h. After removal of the solvent and purification by means of column chromatography, 2-amino-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carboxylic acid tert-butyl ester 5.72 g (43% of theoretical) was obtained.

Workup

  1. temperaturerefluxing
  2. waitwas performed for 5 h
  3. customAfter removal of the solvent and purification by means of column chromatography

Sources & evidence

ORD record
ord-de854265abc74d03ac855410d32f4ee1
Source dataset
uspto-grants-2010_02
Patent number
US07662828B2

Reaction notes

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