HCID 67063149, compound → HCID 67063098, compound

HRID 599261Notes

Reaction equation

HRID 599261 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][C:16]3[C:11](=[N:12][C:13]([S:18][CH3:19])=[N:14][CH:15]=3)[N:10]([CH3:20])[C:9]2=[O:21])=[CH:4][C:3]=1[N+:22]([O-])=O>CO.[Pd]>[NH2:22][C:3]1[CH:4]=[C:5]([N:8]2[CH2:17][C:16]3[C:11](=[N:12][C:13]([S:18][CH3:19])=[N:14][CH:15]=3)[N:10]([CH3:20])[C:9]2=[O:21])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 67063149HCID 67063149, compound

Product 1

HCID 67063098HCID 67063098, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(4-fluoro-3-nitrophenyl)-1-methyl-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (3.0 g, 8.6 mmol) in MeOH (30 mL) was added 10% Pd/C (1.2 g, 1.1 mmol). The resultant mixture was stirred overnight under H2 (30 psi). The mixture was filtered, concentrated in vacuo and purified by silica gel column chromatography to give 3-(3-amino-4-fluorophenyl)-1-methyl-7-(methylthio)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (1.8 g, 66% yield) as a brown solid. 1H NMR (300 MHz, DMSO-d6): δ 8.21 (s, 1 H), 6.99 (dd, J=6.6, 8.4 Hz, 1 H), 6.70 (dd, J=1.8, 6.0 Hz, 1 H), 6.47 (m, 1 H), 5.21 (br s, 2 H), 4.65 (s, 2 H), 3.26 (s, 3 H), 2.50 (s, 3 H); MS (ESI) m/z: 320.0 (M+H+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-6299f3b74b4543d39a3c70b7d8ece0d2
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

Loading…