Sodium Hydroxide → 5-Cyano-4-phenyl-N-(3,4,5-trimethoxyphenyl)pyrimidine-2-amine

HRID 1370066Notes

Reaction equation

HRID 1370066 reaction equation
[N+]([O-])([O-])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([NH:17][C:18]([NH2:20])=[NH2+:19])[CH:10]=[C:11]([O:15][CH3:16])[C:12]=1[O:13][CH3:14].[C:21]1([C:27](=O)[C:28]([C:33]#N)=[CH:29][N:30](C)C)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+]>C(O)C>[C:29]([C:28]1[C:27]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:19][C:18]([NH:17][C:9]2[CH:10]=[C:11]([O:15][CH3:16])[C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=2)=[N:20][CH:33]=1)#[N:30]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 38455902-[(Dimethylamino)methylene]-3-oxo-3-phenylpropanenitrileHCID 178419082HCID 178419082, compound

Product 1

HCID 98203645-Cyano-4-phenyl-N-(3,4,5-trimethoxyphenyl)pyrimidine-2-amineYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3,4,5-trimethoxyphenylguanidinium nitrate (1.44 g, 5.0 mmol), 1-phenyl-2-cyano-3-dimethylaminopropen-1-one (1.0 g, 5.0 mmol) and sodium hydroxide (0.22 g, 5.5 mmol) in ethanol (20 ml) was heated at reflux for 18 h. On cooling the resulting precipitate was collected by filtration, washed with water and diethyl ether, then dried to give the title compound (895 mg) as a green solid m.p. 246°. δH (d6DMSO) 10.37 (1H, br s), 8.93 (1H, s), 7.99 (2H, m), 7.60 (3H, m), 7.25 (2H, m), 3.75 (6H, s) and 3.63 (3H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. temperatureOn cooling the resulting precipitate
  4. filtrationwas collected by filtration
  5. washwashed with water and diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-ae90bc59464b4eb090e95ada81b2db1f
Source dataset
uspto-grants-2003_06
Patent number
US06579983B1

Reaction notes

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