HCID 86629442, compound → HCID 67063014, compound

HRID 599285Notes

Reaction equation

HRID 599285 reaction equation
[CH2:1]([N:3]1[C:8]2[CH:9]=[C:10]([N:13](OC)[CH3:14])[N:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:17]2[CH:22]=[C:21]([N+:23]([O-])=O)[C:20]([F:26])=[CH:19][C:18]=2[CH3:27])[C:4]1=[O:28])[CH3:2].[H][H]>CO.[Pd]>[NH2:23][C:21]1[C:20]([F:26])=[CH:19][C:18]([CH3:27])=[C:17]([N:5]2[CH2:6][C:7]3[CH:12]=[N:11][C:10]([NH:13][CH3:14])=[CH:9][C:8]=3[N:3]([CH2:1][CH3:2])[C:4]2=[O:28])[CH:22]=1

Participants

5

Reactant 2

HCID 86629442HCID 86629442, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67063014HCID 67063014, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Ethyl-3-(4-fluoro-2-methyl-5-nitrophenyl)-7-(methoxy(methyl)amino)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (3.2 g, 8.2 mmol) and Pd/C (0.3 g) were combined in MeOH (60 ml) and subjected to hydrogen (45 psi) at 50° C. overnight. The reaction mixture was filtered, concentrated in vacuo and purified by column chromatography to give 3-(5-amino-4-fluoro-2-methylphenyl)-1-ethyl-7-(methylamino)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (2.1 g, 78% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.71 (s, 1 H), 6.88 (d, J=12.0 Hz, 1 H), 6.64 (d, J=8.4 Hz, 1 H), 6.38 (m, 1 H), 5.99 (s, 1 H), 5.01 (s, 2 H), 4.51 (d, J=13.6 Hz, 1 H), 4.29 (d, J=13.6 Hz, 1 H), 3.76 (m, 2 H), 2.75 (d, J=4.8 Hz, 3 H), 1.91 (s, 3 H), 1.14 (t, J=7.2 Hz, 3 H); MS (ESI) m/z: 330.2 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-777c63334f184aa28968212f3b0ae770
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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