N,N-Dimethylaniline → 7-Chloro-5-(furan-2-yl)-2-phenylpyrazolo[1,5-a]pyrimidine

HRID 2172560Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:7][C:8]2[N:9]([N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:15]=2)[C:10](=O)[CH:11]=1.O=P(Cl)(Cl)[Cl:24].CN(C)C1C=CC=CC=1>C(#N)C.C(Cl)(Cl)Cl>[Cl:24][C:10]1[N:9]2[N:13]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:15]=[C:8]2[N:7]=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-(furan-2-yl)-2-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one (0.277 g, 1.0 mmol, 1.0 eq), POCl3 (0.613 g, 4.0 mmol, 4.0 eq), N-benzyl-N,N,N-triethylethanaminium chloride (0.456 g, 2.0 mmol, 2.0 eq) and N,N-dimethylaniline (0.121 g, 1.0 mmol, 1.0 eq) in acetonitrile (5.0 mL) was heated at 80° C. for 4 hr. The completed reaction was diluted with CHCl3 (20 mL), washed with H2O (10 mL), and the separated organic layers were dried (MgSO4) and concentrated. The residue was purified by chromatography (Biotage25 g, EtOAc/Hexane) to afford 7-chloro-5-(furan-2-yl)-2-phenylpyrazolo[1,5-a]pyrimidine (0.247 g, 84%) as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ 7.97-7.94 (m, 2H), 7.56 (m, 1H), 7.43-7.39 (m, 2H), 7.36-7.34 (m, 1H), 7.19 (s, 1H), 7.17 (dd, J=3.5, 0.5 Hz, 1H), 6.97 (s, 1H), 6.54 (dd, J=3.5, 1.7 Hz, 1H).

Workup

customThe completed reaction
washwashed with H2O (10 mL)
dry with materialthe separated organic layers were dried (MgSO4)
concentrationconcentrated
customThe residue was purified by chromatography (Biotage25 g, EtOAc/Hexane)

Sources & evidence

ORD record: ord-d6c5ddc124244468ba21727318ed4c30
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056111B1

Reaction notes

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