HCID 67063139, compound → HCID 67063099, compound

HRID 599272Notes

Reaction equation

HRID 599272 reaction equation
[CH2:1]([N:3]1[C:8]2=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=[C:7]2[CH2:6][N:5]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([N+:22]([O-])=O)[CH:16]=2)[C:4]1=[O:25])[CH3:2]>C(OCC)(=O)C.CO.[Pd]>[NH2:22][C:17]1[CH:16]=[C:15]([N:5]2[CH2:6][C:7]3[C:8](=[N:9][C:10]([S:13][CH3:14])=[N:11][CH:12]=3)[N:3]([CH2:1][CH3:2])[C:4]2=[O:25])[CH:20]=[CH:19][C:18]=1[F:21]

Participants

5

Reactant 1

HCID 67063139HCID 67063139, compound

Product 1

HCID 67063099HCID 67063099, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-ethyl-3-(4-fluoro-3-nitrophenyl)-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (2.4 g, 6.5 mmol) in ethyl acetate and methanol (1:1, 40 mL) was added Pd/C (230 mg) and the mixture was hydrogenated (55 psi) in a Parr shaker for 2 days. The reaction mixture was filtered and the filter cake was washed with methanol. The combined filtrates were concentrated in vacuo. The residue was dissolved in THF and the solid was filtered. The filtrate was concentrated and purified by silica gel column chromatography to obtain 3-(3-amino-4-fluorophenyl)-1-ethyl-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (0.65 g, 30% yield). 1H-NMR (400 MHz, DMSO-d6): δ 8.20 (s, 1 H), 6.97 (m, 1 H), 6.70 (dd, J=8.0, 2.4 Hz, 1 H), 6.46 (m, 1 H), 5.21 (s, 2 H), 4.64 (s, 2 H), 3.94 (q, J=6.8 Hz, 2 H), 2.48 (s, 3 H), 1.15 (t, J=6.8 Hz, 3 H); MS (ESI) m/z: 334.1 (M+H+).

Workup

  1. customfor 2 days
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake was washed with methanol
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. dissolutionThe residue was dissolved in THF
  6. filtrationthe solid was filtered
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-089d6d49669647a39dbb1c929b3415b5
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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