Phosphorus oxychloride → HCID 18507445, compound

HRID 1355816Notes

Reaction equation

HRID 1355816 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=O)[C:5]([C:13]#[N:14])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.P(Cl)(Cl)([Cl:18])=O>ClCCl>[NH2:1][C:2]1[N:3]=[C:4]([Cl:18])[C:5]([C:13]#[N:14])=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136401064HCID 136401064, compound

Product 1

HCID 18507445HCID 18507445, compoundYield 4.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the method of Hull (J. Chem. Soc. 1957, 4845), a stirred suspension of 3.26 g (16.1 mmol) 2-amino-4-furan-2-yl-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile in 3.7 ml (40.3 mmol) phosphorus oxychloride was heated at reflux for 90 minutes. The reaction mixture was then cooled to room temperature, diluted with dichloromethane, and poured cautiously onto 100 ml rapidly stirred ice-water such that the temperature remained around 10° C. The phases were separated and the aqueous phase further extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate) afforded 0.16 g (4%) 2-amino-4-chloro-6-furan-2-yl-pyrimidine-5-carbonitrile as an orange crystalline solid. EI-MS m/e (%): 222 (M{37Cl}+, 34), 220 (M{35Cl}+, 100), 143 (30).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 90 minutes
  3. customremained around 10° C
  4. customThe phases were separated
  5. extractionthe aqueous phase further extracted with dichloromethane
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4466a1f064784396968e4a8ed8c5d50d
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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