Ammonia → HCID 22313251, compound

HRID 989725Notes

Reaction equation

HRID 989725 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](O)[C:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:19])=O.N>>[Cl:19][C:6]1[C:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178508388HCID 178508388, compound

Product 1

HCID 22313251HCID 22313251, compoundYield 40.7%

Conditions

Temperature
90 °C

Procedure

A mixture of 2-amino-5-phenethylpyrimidine-4-ol (600 mg, 2.79 mmol) and phosphorous oxychloride (5 ml) was kept to warm at 90° C. for 6 hours. The reaction mixture was condensed in vacuo. Ice-water was added to the residue and an aqueous ammonia was cautiously added thereto. The solution was extracted with chloroform. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (chloroform: ethyl acetate=8:2) to give the object compound (265 mg, 40.7%).

Workup

  1. customcondensed in vacuo
  2. extractionThe solution was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform: ethyl acetate=8:2)

Sources & evidence

ORD record
ord-7d0449b069bb4e2dabf2505fcdc07043
Source dataset
uspto-grants-2002_10
Patent number
US06458798B1

Reaction notes

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