HCID 56851171, compound → HCID 56851285, compound

HRID 1926121Notes

Reaction equation

HRID 1926121 reaction equation
[O:1]([C:8]1[C:9]2[NH:16][C:15]([C:17]([NH2:19])=O)=[CH:14][C:10]=2[N:11]=[CH:12][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>P(Cl)(Cl)(Cl)=O>[O:1]([C:8]1[C:9]2[NH:16][C:15]([C:17]#[N:19])=[CH:14][C:10]=2[N:11]=[CH:12][N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 56851171HCID 56851171, compound

Product 1

HCID 56851285HCID 56851285, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
70 °C

Procedure

4-Phenoxy-5H-pyrrolo[3,2-d]pyrimidine-6-carboxamide (1.67 g) was suspended in phosphorus oxychloride (20 mL), and the suspension was stirred at 70° C. for 3 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in tetrahydrofuran (25 mL). Water and aqueous ammonia were added to the solution, and the mixture was extracted with a mixed solvent of ethyl acetate/tetrahydrofuran=1/1. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→67:33) to give the title compound (1.07 g) as a pale-yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in tetrahydrofuran (25 mL)
  3. additionWater and aqueous ammonia were added to the solution
  4. extractionthe mixture was extracted with a mixed solvent of ethyl acetate/tetrahydrofuran=1/1
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was separated
  9. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=90:10→67:33)

Sources & evidence

ORD record
ord-a5ff2459eea94d37aae29a8db618488e
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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