HCID 68727193, compound → HCID 25235913, compound

HRID 509506Notes

Reaction equation

HRID 509506 reaction equation
[CH3:1][C:2]1[N:11]([CH:12]2[CH2:17][CH2:16][C:15](=[O:18])[NH:14][C:13]2=[O:19])[C:10](=[O:20])[C:9]2[C:4](=[CH:5][C:6]([N+:21]([O-])=O)=[CH:7][CH:8]=2)[N:3]=1>C1CCCCC=1.CN(C=O)C.[OH-].[OH-].[Pd+2]>[NH2:21][C:6]1[CH:5]=[C:4]2[C:9]([C:10](=[O:20])[N:11]([CH:12]3[CH2:17][CH2:16][C:15](=[O:18])[NH:14][C:13]3=[O:19])[C:2]([CH3:1])=[N:3]2)=[CH:8][CH:7]=1

Participants

5

Reactant 1

HCID 68727193HCID 68727193, compound

Product 1

HCID 25235913HCID 25235913, compoundYield 82.5%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 6228DimethylformamideSolventHCID 8079CyclohexeneSolvent

Conditions

Temperature
125 °C

Procedure

A suspension of 3-(2-methyl-7-nitro-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione (4.8 g, 13 mmol) and 20% Pd(OH)2/C (1.0 g) in cyclohexene (15 mL) and DMF (60 mL) was heated in a 125° C. oil bath overnight. The suspension was filtered thru a pad of Celite, and washed with DMF (30 mL). To the filtrate, was added water (150 mL) to give a suspension. The suspension was filtered and washed with water (50 mL) to give 3-(7-amino-2-methyl-4-oxo-4H-quinazolin-3-yl)-piperidine-2,6-dione as an off-white solid (3.07 g, 71% yield): HPLC: Waters Symmetry C18, 5 μm, 3.9×150 mm, 1 mL/min, 240 nm, 5/95 grad 95/5 in 5 min CH3CN/0.1% H3PO4, 4.08 min (97.3%) [sample was dissolved in 0.1% H3PO4]; mp: 305-307° C.; 1H NMR (DMSO-d6) δ 2.05-2.16 (m, 1H, CHH), 2.53 (s, 3H, CH3), 2.58-2.69 (m, 2H, 2CHH), 2.75-2.86 (m, 1H, CHH), 5.10 (dd, J=6, 11 Hz, 1H, NCH), 6.11 (brs, 2H, NH2), 6.54 (d, J=2 Hz, 1H, Ar), 6.68 (dd, J=2, 8 Hz, 1H, Ar), 10.93 (s, 1H, NH); 13C NMR (DMSO-d6) δ 21.36, 23.43, 30.63, 55.97, 106.12, 109.17, 114.70, 127.28, 148.95, 154.42, 154.61, 159.85, 169.87, 172.67; LCMS: MH=287; Anal Calcd for C14H14N4O3: C, 58.74; H, 4.93; N, 19.57. Found: C, 58.60; H, 4.83; N, 19.40.

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with DMF (30 mL)
  3. additionTo the filtrate, was added water (150 mL)
  4. customto give a suspension
  5. filtrationThe suspension was filtered
  6. washwashed with water (50 mL)

Sources & evidence

ORD record
ord-9ddb0dacee9d45db9798584d3abd0aca
Source dataset
uspto-grants-2015_08
Patent number
US09096573B2

Reaction notes

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