Hydrochloric Acid → HCID 86629455, compound

HRID 599298Notes

Reaction equation

HRID 599298 reaction equation
[C:1]([N:5]1[C:10]2[CH:11]=[C:12]([Cl:15])[N:13]=[CH:14][C:9]=2[CH2:8][N:7]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([N+:23]([O-])=O)[CH:17]=2)[C:6]1=[O:26])([CH3:4])([CH3:3])[CH3:2].Cl>[Fe].CCO.O>[NH2:23][C:18]1[CH:17]=[C:16]([N:7]2[CH2:8][C:9]3[CH:14]=[N:13][C:12]([Cl:15])=[CH:11][C:10]=3[N:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:6]2=[O:26])[CH:21]=[CH:20][C:19]=1[F:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86629454HCID 86629454, compound

Product 1

HCID 86629455HCID 86629455, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
40 °C

Procedure

Iron powder was added (5.2 g, 93 mmol) in portions to a solution of 1-tert-butyl-7-chloro-3-(4-fluoro-3-nitrophenyl)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (3.5 g, 9.3 mmol) and conc. HCl (0.35 mL, 4.2 mmol) in 10/1 EtOH/H2O (11 mL). The resulting mixture was stirred at 40° C. for 30 min. The reaction mixture was filtered and the filter cake was washed with EtOH. The ethanolic filtrate was concentrated and the residue was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (3×80 mL). The combined organics were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by chromatography on silica gel to afford 3-(3-amino-4-fluorophenyl)-1-tert-butyl-7-chloro-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (2.0 g, 62% yield). 1HNMR (400 MHz, DMSO-d6): δ 8.20 (s, 1 H), 7.26 (s, 1 H), 6.92 (m, 1 H), 6.62 (m, 1 H), 6.34 (m, 1 H), 5.17 (s, 2 H), 4.50 (s, 2H), 1.55 (s, 9 H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake was washed with EtOH
  3. concentrationThe ethanolic filtrate was concentrated
  4. customthe residue was partitioned between EtOAc and H2O
  5. extractionThe aqueous layer was extracted with EtOAc (3×80 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-8e80c59f22424538aa947730d8dbbaa4
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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