2,5-Pyridinediamine → HCID 178512279, compound
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][N:3]=1.[CH:9]1[CH:14]=[CH:13][C:12]([O:15][C:16](OC2C=CC=CC=2)=[N:17][C:18]#[N:19])=[CH:11][CH:10]=1>COCCOC>[C:18]([N:17]=[C:16]([O:15][C:12]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1)[NH:8][C:5]1[CH:4]=[N:3][C:2]([NH2:1])=[CH:7][CH:6]=1)#[N:19]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred mixture of the crude 2,5-diaminopyridine from Step 1 (0.0719 mol) and 100 ml of ethylene glycol dimethylether, under nitrogen, was added diphenylcyanocarbonimidate (17.1 g, 0.0718 mol) in one portion. This mixture was stirred at room temperature for 5 hours and concentrated in vacuo. The residue was triturated three times with Et2O. The solid residue (17.5 g) was stored under nitrogen until it was chromatographed in two portions: 5.0 g was chromatographed over 1000 ml of silica gel (230-400 mesh) by gravity elution with 5% MeOH/CHCl3 at a rate of 21 ml/minute to give 3.02 g of product; the other 12.5 g was chromatographed over 1000 ml of silica gel in the same manner (a poorer separation resulted at this loading) to give 7.31 g of product. The two lots were combined and crystallized from CH3CN to give 8.32 g (45.8%), m.p. 191°-192.5° C. of the titled product as amber needles. (An additional 0.98 g (5.4%) of dark amber needles was also obtained.)
Workup
- concentrationconcentrated in vacuo
- customThe residue was triturated three times with Et2O
- customwas chromatographed in two portions
- custom5.0 g was chromatographed over 1000 ml of silica gel (230-400 mesh) by gravity elution with 5% MeOH/CHCl3 at a rate of 21 ml/minute
Sources & evidence
- ORD record
- ord-92da4bbd656e4043b049e608cacbce7e
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05567722
Reaction notes
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