Sodium Hydroxide → HCID 18516888, compound

HRID 1370094Notes

Reaction equation

HRID 1370094 reaction equation
[C:1]([C:3](=[CH:11]N(C)C)[C:4]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)=O)#[N:2].[N+]([O-])([O-])=O.[N+:19]([C:22]1[CH:23]=[C:24]([NH:28][C:29]([NH2:31])=[NH2+:30])[CH:25]=[CH:26][CH:27]=1)([O-:21])=[O:20].[OH-].[Na+]>>[C:1]([C:3]1[C:4]([C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)=[N:30][C:29]([NH:28][C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)=[N:31][CH:11]=1)#[N:2]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 3743025α-[(Dimethylamino)methylene]-β-oxo-2-thiophenepropanenitrileHCID 178512439HCID 178512439, compound

Product 1

HCID 18516888HCID 18516888, compound

Procedure

5-Cyano-N-3-nitrophenyl-4-thien-2-ylpyrimidine-2-amine was prepared from 2-cyano-3-dimethylamino-1-thien-2-ylpropen-1-one (3.20 g, 15.51 mmol), 3-nitrophenylguanidinium nitrate (3.74 g, 15.53 mmol) and sodium hydroxide (652 mg, 7.82 mmol) to give the desired material (841 mg) as an off-white solid, m.p.275-277°. δH (d6 DMSO) 10.87 (1H, bs), 8.98 (1H, s), 8.90 (1H, bs), 8.31-8.29 (1H, m), 8.09-8.05 (2H, m), 7.91 (1H, dd, J 7.7,2.0 Hz), 7.64 (1H, t ,J 8.1 Hz) and 7.37-7.35 (1H, m).

Sources & evidence

ORD record
ord-4c3a10b3d55e47e2b2a0f390b41670d9
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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