Hydrochloric Acid → HCID 178509388, compound

HRID 1355954Notes

Reaction equation

HRID 1355954 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]#[N:14])=[C:4]([S:15]C)[N:3]=1.O.Cl>C(O)C>[NH2:1][C:2]1[NH:3][C:4](=[S:15])[C:5]([C:13]#[N:14])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 12451273HCID 12451273, compound

Product 1

HCID 178509388HCID 178509388, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1.1 g (4.74 mmol) 2-amino-4-(2-furyl)-6-(methylthio)-pyrimidine-5-carbonitrile in 15 ml ethanol under argon was added 1.05 g (14.2 mmol) sodium thiolate and the mixture heated at reflux for 16 h. The reaction mixture was then cooled to room temperature, 20 ml water added, and the mixture made slightly acidic by dropwise addition of concentrated hydrochloric acid. The resulting crystals were collected by filtration, washed with water, and dried in vacuo to afford 0.90 g (87%) 2-amino-4-furan-2-yl-6-thioxo-1,6-dihydro-pyrimidine-5-carbonitrile as a yellow crystalline solid. ES-MS m/e (%): 217 ([M—H]−, 100).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 16 h
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-61f669b0cff94ecfb0dc1595dc366b22
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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