HCID 86629449, compound → HCID 67063112, compound

HRID 599292Notes

Reaction equation

HRID 599292 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]=[CH:21][C:20]([F:23])=[C:19]([N+:24]([O-])=O)[CH:18]=2)[C:4]1=[O:27])[CH3:2].[H][H]>CO.[Pd]>[NH2:24][C:19]1[CH:18]=[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:27])[CH:22]=[CH:21][C:20]=1[F:23]

Participants

5

Reactant 2

HCID 86629449HCID 86629449, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67063112HCID 67063112, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Ethyl-3-(4-fluoro-3-nitrophenyl)-7-(methoxy(methyl)amino)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (4.6 g, 12 mmol), Pd/C (0.5 g) and hydrogen (45 psi) were reacted in MeOH (100 mL) at 50° C. overnight to give 3-(3-amino-4-fluorophenyl)-1-ethyl-7-(methylamino)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (3.2 g, 84%). 1H-NMR (400 MHz, DMSO-d6): δ 7.70 (s, 1 H), 6.94 (dd, J=11.2, 8.8 Hz, 1 H), 6.67 (dd, J=8.0, 2.4 Hz, 1 H), 6.42 (m, 1 H), 6.33 (m, 1 H), 5.98 (s, 1 H), 5.14 (s, 2 H), 4.48 (s, 2 H), 3.74 (q, J=7.2 Hz, 2 H), 2.73 (d, J=5.2 Hz, 3 H), 1.15 (t, J=7.2 Hz, 3 H); MS (ESI) m/z: 316.2 [M+H]+.

Sources & evidence

ORD record
ord-4e0a287bed664b44913dcf2d58e11a3d
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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