HCID 86629459, compound → HCID 67063053, compound

HRID 599304Notes

Reaction equation

HRID 599304 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[N:12]1[CH2:17][C:16]2[CH:18]=[N:19][C:20]([N:22](OC)[CH3:23])=[CH:21][C:15]=2[N:14]([CH2:26][CH3:27])[C:13]1=[O:28].[H][H]>[Pd]>[NH2:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([Cl:1])=[C:3]([N:12]2[CH2:17][C:16]3[CH:18]=[N:19][C:20]([NH:22][CH3:23])=[CH:21][C:15]=3[N:14]([CH2:26][CH3:27])[C:13]2=[O:28])[CH:4]=1

Participants

4

Reactant 2

HCID 86629459HCID 86629459, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67063053HCID 67063053, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3-(2-Chloro-4-fluoro-5-nitrophenyl)-1-ethyl-7-(methoxy(methyl)amino)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (2.7 g, 6.6 mmol), Pd/C (1.4 g) and hydrogen (30 psi) were combined at 45° C. by the procedure of Example A4 to provide 3-(5-amino-2-chloro-4-fluorophenyl)-1-ethyl-7-(methylamino)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (2 g, 87.0% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.72 (s, 1 H), 7.24 (d, J=10.8 Hz, 1 H), 6.81 (d, J=9.2 Hz, 1 H), 6.44 (bs, 1 H), 6.02 (s, 1 H), 5.42 (s, 2 H), 4.50 (d, J=13.2 Hz, 1 H), 4.38 (d, J=13.2 Hz, 1 H), 3.77 (m, 2 H), 2.76 (d, J=4.8 Hz, 3 H), 1.15 (t, J=7.2 Hz, 3 H); MS (ESI) m/z: 350.2[M+H]+.

Workup

  1. customwere combined at 45° C. by the procedure of Example A4

Sources & evidence

ORD record
ord-ad99103749214b03b8688716d4960836
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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