HCID 56851171, compound → HCID 56851285, compound

HRID 1787035Notes

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

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 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

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

Sources & evidence

ORD record: ord-f8ac4050ac0942b3a95d6783bc28672a
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507740B2

Reaction notes

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