Acetic Acid → 2-Amino-4-chloro-6-oxo-1,6-dihydropyrimidine-5-carbonitrile

HRID 1356115Notes

Reaction equation

HRID 1356115 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[C:7](Cl)[C:6]([CH:10]=[N:11]O)=[C:5]([Cl:13])[N:4]=1.C(O)(=[O:16])C>>[NH2:2][C:3]1[NH:8][C:7](=[O:16])[C:6]([C:10]#[N:11])=[C:5]([Cl:13])[N:4]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 731656572-Amino-4,6-dichloro-pyrimidine-5-carbaldehyde oxime

Product 1

HCID 1356048692-Amino-4-chloro-6-oxo-1,6-dihydropyrimidine-5-carbonitrileYield 93%

Conditions

Temperature
115 °C

Procedure

Following the method of Bell et al. (J. Heterocyclic Chem. 1983, 20, 41), hydrogen chloride gas was bubbled for 2 minutes though a solution of 6.00 g (29.0 mmol) 2-amino-4,6-dichloro-pyrimidine-5-carbaldehyde oxime in 800 ml acetic acid at 115° C. The mixture was then stirred at 115° C. for 16 hours before being cooled to room temperature. The resulting crystals were removed by filtration, and the filtrate concentrated in vacuo. The residue was triturated in 100 ml ether to afford 4.60 g (93%) 2-amino-4-chloro-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile as a light yellow crystalline solid. EI-MS m/e (%): 172 (M{37Cl}+, 23), 170 (M{35Cl}+, 71), 129 (53), 43 (100).

Workup

  1. temperaturebefore being cooled to room temperature
  2. customThe resulting crystals were removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was triturated in 100 ml ether

Sources & evidence

ORD record
ord-13a4ebe5d7aa4fa1abad46c89552eef2
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

Loading…