Sodium Bicarbonate → 5-(4-Chloro-phenyl)-6-[4-(6-oxo-1,6-dihydro-pyridin-3-yl)-phenyl]-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1693553Notes

Reaction equation

HRID 1693553 reaction equation
N[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:15]([C:30]4[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=4)[C:16](=[O:29])[C:17]4[CH:22]=[N:21][N:20]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[C:18]=4[N:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.N([O-])=[O:38].[Na+].C([O-])(O)=O.[Na+]>C(#N)C.O.OS(O)(=O)=O>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([N:15]2[C:16](=[O:29])[C:17]3[CH:22]=[N:21][N:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:18]=3[N:19]=[C:14]2[C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[CH:3][C:2](=[O:38])[NH:7][CH:6]=3)=[CH:9][CH:10]=2)=[CH:35][CH:34]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 578979376-[4-(6-Amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 578979515-(4-Chloro-phenyl)-6-[4-(6-oxo-1,6-dihydro-pyridin-3-yl)-phenyl]-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-[4-(6-amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (28.1 mg, 0.057 mmol) in acetonitrile (0.5 mL) is added a solution of NaNO2 (5.4 mg, 0.078 mmol) in H2O (0.5 mL) at 0° C., followed by addition of one drop of concentrated H2SO4. The reaction mixture is then heated at 100° C. for 30 minutes, cooled down to 0° C., neutralized by saturated NaHCO3 to pH= 4-5, and extracted with ethyl acetate. The organic layer is concentrated and purified by preparative LC/MS to provide the title compound; 1H NMR (CDCl3, 400 MHz) δ 8.34 (s, 1H), 8.14 (d, 2H), 7.91 (dd, 1H), 7.75 (d, 1H), 7.52 (t, 2H), 7.44 (d, 2H), 7.36 (m, 5H), 7.13 (d, 2H), 6.88 (d, 1H); HPLC-MS calculated for C28H18ClN5O2 (M+H+) 492.1. Found: 492.1.

Workup

  1. temperaturecooled down to 0° C.
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer is concentrated
  4. custompurified by preparative LC/MS

Sources & evidence

ORD record
ord-726feba875b143278dcb2443ea896281
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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