Phosphorus oxychloride → HCID 57898035, compound

HRID 1693560Notes

Reaction equation

HRID 1693560 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[C:15]([C:24]([NH2:26])=O)=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:27]2[CH:32]=[CH:31][C:30]([CH:33]([CH3:35])[CH3:34])=[CH:29][CH:28]=2)=[CH:4][CH:3]=1.ClC1C=CC(N2C(=O)C3C(C(O)=O)=NN(C4C=CC=CC=4)C=3N=C2C2C=CC(C(C)C)=CC=2)=CC=1.O=P(Cl)(Cl)Cl>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13](=[O:14])[C:12]3[C:15]([C:24]#[N:26])=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:27]2[CH:28]=[CH:29][C:30]([CH:33]([CH3:35])[CH3:34])=[CH:31][CH:32]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 57898067HCID 57898067, compoundHCID 67282062HCID 67282062, compound

Product 1

HCID 57898035HCID 57898035, compound

Procedure

5-(4-Chloro-phenyl)-6-(4-isopropyl-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid amide (10 mg, 0.021 mmol; prepared from 5-(4-chloro-phenyl)-6-(4-isopropyl-phenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid following the procedure as in example 342) is treated with POCl3 at 80° C. for 30 min. The mixture is then cooled down to room temperature and concentrated under vacuum. The residue is treated with sat. aqueous NaHCO3 solution (1 mL) and extrated with EtOAc. The combined extracts is then concentrated and purified by preparative thin layer chromatography (silica gel, 30% EtOAc/hexane) to provide the title compound 5-(4-Chloro phenyl)-6-(4-isopropylphenyl)-4-oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carbonitrile as white solid. 1H NMR (CDCl3) δ (ppm) 8.13(d, 2H), 7.54(t, 2H), 7.44(t, 1H), 7.33(d,2H), 7.25(d, 2H), 7.10(m, 4H), 2.87(m, 1H), 1.20(d, 6H). HPLC-MS calculated C27H20ClN5O (M+1+): 466.1. Found: 466.1.

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe residue is treated with sat. aqueous NaHCO3 solution (1 mL)
  3. concentrationThe combined extracts is then concentrated
  4. custompurified by preparative thin layer chromatography (silica gel, 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-9e92b511e51048ec8d7b8e4da2054670
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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