Water → HCID 12451271, compound

HRID 1355689Notes

Reaction equation

HRID 1355689 reaction equation
[C:1]([C:9](=[C:12](SC)[S:13][CH3:14])[C:10]#[N:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([O-])(O)=O.[NH2:21][C:22]([NH2:24])=[NH:23].C(N(CC)CC)C.O>CN(C=O)C>[NH2:24][C:22]1[N:23]=[C:12]([S:13][CH3:14])[C:9]([C:10]#[N:11])=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10481Guanidine NitrateHCID 28190822-Benzoyl-3,3-di(methylthio)acrylonitrile

Product 1

HCID 12451271HCID 12451271, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the method of Rudorf and Augustin (J. Prakt. Chem. 1978, 320, 576), a solution of 15.9 g (63.9 mmol) 2-benzoyl-3,3-bis(methylthio)acrylonitrile, 9.36 g (76.7 mmol) guanidine nitrate and 22.3 ml (160 mmol) triethylamine in 200 ml DMF was heated at reflux for 6 h. The reaction mixture was then cooled to room temperature. On addition of 300 ml water, a precipitate appeared which was collected by filtration and washed with water to afford 12.7 g (86%) 2-amino-4-(methylthio)-6-phenyl-pyrimidine-5-carbonitrile as a sand-coloured solid. EI-MS m-e (%): 242 (M+, 32), 241 ([M—H]+, 100).

Workup

  1. temperatureat reflux for 6 h
  2. filtrationwas collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-80bdab638ca54205ae2d09b9944d6466
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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