2-amino-6-(4-fluoro-3-nitrophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-one → 2-amino-6-(3-amino-4-fluorophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1930314Notes

Reaction equation

HRID 1930314 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([N+:19]([O-])=O)[CH:13]=3)[C:9](=[O:22])[N:8]([CH:23]([CH3:25])[CH3:24])[C:6]=2[N:7]=1>CCOC(C)=O.CO.[Pd]>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[C:14]([NH2:19])[CH:13]=3)[C:9](=[O:22])[N:8]([CH:23]([CH3:25])[CH3:24])[C:6]=2[N:7]=1

Participants

5

Reactant 1

HCID 692975172-amino-6-(4-fluoro-3-nitrophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 689861172-amino-6-(3-amino-4-fluorophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-oneYield 72.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-6-(4-fluoro-3-nitrophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-one (0.52 g, 1.5 mmol) in EtOAc and methanol (5:1, 30 mL) was added palladium on carbon (50 mg of 10% mol) and mixture was stirred under a hydrogen atmosphere at RT for 16 h. The mixture was filtered over a Celite pad and the pad was washed with EtOAc (2×10 mL). The combined filtrate was concentrated in vacuo to provide crude product. Purification by silica gel chromatography afforded 2-amino-6-(3-ammo-4-fluorophenyl)-8-isopropylpyrido[2,3-d]pyrimidin-7(8H)-one as an off-white solid (0.34 g, 72% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.60 (s, 1H), 7.73 (s, 1H), 7.22 (s, 2H), 7.08 (dd, J=9.2 Hz, 1.2 Hz, 1H), 6.99 (dd, J=10.8 Hz, 8.4 Hz, 1H), 6.74-6.70 (m, 1H), 5.78-5.76 (m, 1H), 5.13 (s, 2H), 1.53 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 314.0 (M+H+).

Workup

  1. filtrationThe mixture was filtered over a Celite pad
  2. washthe pad was washed with EtOAc (2×10 mL)
  3. concentrationThe combined filtrate was concentrated in vacuo
  4. customto provide crude product
  5. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-dcf9a72b13a7458cb496c1d4233bb84a
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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