HCID 86629441, compound → HCID 67063026, compound

HRID 599283Notes

Reaction equation

HRID 599283 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]([CH3:26])[C:13]1=[O:27]>CO.[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]([CH3:26])[C:13]2=[O:27])[CH:4]=1

Participants

4

Reactant 1

HCID 86629441HCID 86629441, compound

Product 1

HCID 67063026HCID 67063026, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-(2-chloro-4-fluoro-5-nitrophenyl)-7-(methoxy(methyl)amino)-1-methyl-3,4-dihydro pyrido[4,3-d]pyrimidin-2(1H)-one (1 g, 2.5 mmol), Pd/C (0.3 g) were combined in MeOH (30 mL) and hydrogenated (45 psi) at 50° C. for 4 days. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residual solid was washed with ethyl acetate and dried in vacuo to give 3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-7-(methylamino)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (0.6 g, 71% yield). 1H-NMR (400 MHz, DMSO-d6): δ 7.71 (s, 1 H), 7.26 (d, J==10.8 Hz, 1 H), 6.78 (d, J=8.8 Hz, 1 H), 6.41 (m, 1 H), 5.94 (s, 1 H), 5.43 (s, 2 H), 4.50 (d, J=13.6 Hz, 1 H), 4.40 (d, J=13.6 Hz, 1 H), 3.16 (s, 3 H), 2.76 (d, J=5.2 Hz, 3 H); MS (ESI) m/z: 336.2 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. washThe residual solid was washed with ethyl acetate
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5a2b0f8198c8429f962a0b769e2e07ac
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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