1,2-Dichloroethane → HCID 86084758, compound

HRID 1925952Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:17][C:16]3[C:15](O)=[N:14][CH:13]=[N:12][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.[Cl:19]CCCl.P(Cl)(Cl)(Cl)=O.N>C(N(CC)C1C=CC=CC=1)C.O1CCCC1>[Cl:19][C:15]1[C:16]2[NH:17][C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[CH:10][C:11]=2[N:12]=[CH:13][N:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

6-(4-Methoxyphenyl)-5H-pyrrolo[3,2-d]pyrimidin-4-ol (500 mg) was suspended in N,N-diethylaniline (1.11 mL)/1,2-dichloroethane (3.73 mL), phosphorus oxychloride (2.29 mL) was added, and the mixture was stirred with heating at 110° C. for 2 hrs. After cooling to room temperature, the reaction mixture was treated with ice water (20 mL), and adjusted to pH 7 or above with aqueous ammonia. After diluting with tetrahydrofuran (500 mL), the mixture was washed with saturated brine (50 mL). The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→20:80) to give the title compound (25 mg).

Workup

additionwas added
temperatureAfter cooling to room temperature
washthe mixture was washed with saturated brine (50 mL)
dry with materialThe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was separated
custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=80:20→20:80)

Sources & evidence

ORD record: ord-fa99d01dd69341f8985117dd382a1da5
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178543B2

Reaction notes

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