Morpholine → HCID 11583894, compound

HRID 1693520Notes

Reaction equation

HRID 1693520 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[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:24]2[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[NH:83]1[CH2:88][CH2:87][O:86][CH2:85][CH2:84]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[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:24]2[CH:29]=[CH:28][C:27]([N:83]3[CH2:88][CH2:87][O:86][CH2:85][CH2:84]3)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 57898135HCID 57898135, compound

Product 1

HCID 11583894HCID 11583894, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A reaction tube charged with 5-(4-chlorophenyl)-6-(4-iodo-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (100.0 mg, 0.191 mmol), Pd2(dba)3 (17.5 mg, 0.019 mmol), BINAP (23.7 mg, 0.038 mmol), and Cs2CO3 (124.2 mg, 0.381 mmol) is purged with nitrogen. Anhydrous toluene (1.0 mL) and morpholine (33.2 μL, 0.381 mmol) are added via syringe. The reaction mixture is heated at 100° C. overnight, and is partitioned between water and ethyl acetate. The organic phase is washed with brine, dried over MgSO4, concentrated, and purified by silica gel chromatography to provide the title compound (64.3 mg, 70% yield) as a yellow solid product; 1H NMR (CDCl3, 400 MHz) δ 8.29 (s, 1H), 8.17 (dd, 2H), 7.50 (t, 2H), 7.35 (m, 3H), 7.28 (d, 2H), 7.12 (d, 2H), 6.77 (d, 2H), 3.86 (t, 4H), 3.21 (t, 4H); HPLC-MS calculated for C27H22ClN5O2 (M+H+) 484.1. Found 484.1.

Workup

  1. customis purged with nitrogen
  2. customis partitioned between water and ethyl acetate
  3. washThe organic phase is washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-4d889d8954994b048a249bfaa47b4a80
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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