Sulfuric Acid → HCID 57897964, compound

HRID 1693576Notes

Reaction equation

HRID 1693576 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[N:18]=[CH:19][N:20]([C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)[C:21]=4[N:22]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.N([O-])=[O:38].[Na+].OS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.O>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([N:15]2[C:16](=[O:29])[C:17]3[N:18]=[CH:19][N:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:21]=3[N:22]=[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:31][CH:32]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 57897833HCID 57897833, compound

Product 1

HCID 57897964HCID 57897964, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 2-[4-(6-amino-pyridin-3-yl)-phenyl]-1-(4-chloro-phenyl)-9-phenyl-1,9-dihydro-purin-6-one (10 mg, 0.02 mmol) in acetonitrile (0.4 mL) and H2O (0.4 mL) was treated with NaNO2 and 5 μL of concentrated H2SO4. The reaction mixture was heated at 100° C. for 1 h. The reaction was allowed to cool to room temperature and neutralized with aqueous Na2CO3. The reaction was diluted with H2O and extracted with EtOAc. The combined organics were dried (MgSO4), filtered, and concentrated. The resulting crude material was purified by preparative LCMS to provide the title compound 1-(4-chloro-phenyl)-2-[4-(6-oxo-1,6-dihydro-pyridin-3-yl)-phenyl]-9-phenyl-1,9-dihydro-purin-6-one_as a white solid. 1H NMR (CDCl3) δ (ppm) 8.21 (s, 1H), 8.01 (dd, 1H), 7.81 (d, 1H), 7.58 (apparent t, 2H), 7.49 (m, 1H), 7.39 (d, 2H), 7.33 (m, 3H), 7.14 (d, 2H), 6.98 (d, 1H); HPLC-MS calculated for C28H18ClN5O2 (M+H+): 492.1. Found: 492.1.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude material was purified by preparative LCMS

Sources & evidence

ORD record
ord-5287f2703e0a4c0b80aff18acc791865
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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