N2,N2-dimethylpyridine-2,5-diamine → HCID 42625838, compound

HRID 1668793Notes

Reaction equation

HRID 1668793 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[N:3]=1.[CH3:13][N:14]([CH3:22])[C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][N:16]=1.C([O-])(=O)C.[Na+]>>[CH3:13][N:14]([CH3:22])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:12])[N:3]=2)=[CH:17][N:16]=1

Participants

4

Reactant 3

HCID 78642N2,N2-dimethylpyridine-2,5-diamineHCID 517045Sodium AcetateHCID 27854214-Chloro-2-methylquinazoline

Product 1

HCID 42625838HCID 42625838, compound

Procedure

To a solution of 2-dimethylamino-5-nitropyridine (334 mg, 2 mmol) in 100 ml of methanol was added 5% Pd/C (100 mg, 0.94 mmol). The reaction mixture was hydrogenated under 45 psi at room temperature for 2 h, then it was filtered through a layer of celite (2.5 in d×2 in h) and washed with additional methanol (25 ml). The organic filtrate was concentrated to yield 200 mg (73%) of 2-dimethylamino-5-amino-pyridine as dark brown sticky solids. The title compound was prepared from 4-chloro-2-methyl-quinazoline (182.2 mg, 1.02 mmol), 2-dimethylamino-5-amino-pyridine (140 mg, 1.02 mmol) and sodium acetate (98.4 mg, 1.2 mmol) similar to example 20 to give 60 mg (21%) of paint yellow solids. 1H NMR (CDCl3): 8.43 (d, J=2.4 Hz, 1H), 7.95 (dd, J=2.7 Hz, J=9.3 Hz, 1H), 7.84-7.72 (m, 3H), 7.47 (t, J=8.1 Hz, 1H), 7.16 (brs, 1H), 6.61 (d, J=9.0 Hz, 1H), 3.12 (s, 6H), 2.65 (s, 3H).

Workup

  1. customto give 60 mg (21%) of paint yellow solids

Sources & evidence

ORD record
ord-bd776bd0d33f4e83a1732b6d2d537a94
Source dataset
uspto-grants-2011_08
Patent number
US07989462B2

Reaction notes

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