3,4-Diaminopyridine → HCID 21779135, compound

HRID 2172851Notes

Reaction equation

HRID 2172851 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].[C:9](OCC)(=[O:13])[C:10]([CH3:12])=O>C(Cl)(Cl)Cl>[CH3:12][C:10]1[C:9](=[O:13])[NH:1][C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 59183,4-DiaminopyridineHCID 12041Ethyl pyruvate

Product 1

HCID 21779135HCID 21779135, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 3,4-diamino pyridine (10 g) and ethyl pyruvate (53 g) in chloroform (100 mL) was stirred at ambient temperature overnight. The precipitated solid was filtered off, washed with DCM, and dried to afford 2-methyl-4H-pyrido[3,4-b]pyrazin-3-one (14 g) as a yellowish solid. 2 g of this material was suspended in DMF (10 mL) and treated with PyBroP (6 g) and DIPEA (3.3 mL,) at ambient temperature overnight. The precipitated solid was filtered off, washed with ethanol, and dried to afford 3-(benzotriazol-1-yloxy)-2-methyl-pyrido[3,4-b]pyrazine (1.7 g) as a white solid. This material was suspended in ethanol (50 mL), hydrazine hydrate was added, and resulting mixture was heated at 85° C. for 15 min. The solid was filtered off, washed with ethanol, and dried to afford IIc (0.95 g) as a yellow solid sufficiently pure for the next step.

Workup

  1. filtrationThe precipitated solid was filtered off
  2. washwashed with DCM
  3. customdried

Sources & evidence

ORD record
ord-7e983733836f4e9da595e6f7b0954e91
Source dataset
uspto-grants-2015_06
Patent number
US09056863B2

Reaction notes

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