HCID 86629437, compound → HCID 67062977, compound

HRID 599265Notes

Reaction equation

HRID 599265 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][C:12]3[CH:14]=[N:15][C:16]([N:18](OC)[CH3:19])=[CH:17][C:11]=3[N:10]([CH3:22])[C:9]2=[O:23])=[CH:4][C:3]=1[N+:24]([O-])=O>CO.[Pd]>[NH2:24][C:3]1[CH:4]=[C:5]([N:8]2[CH2:13][C:12]3[CH:14]=[N:15][C:16]([NH:18][CH3:19])=[CH:17][C:11]=3[N:10]([CH3:22])[C:9]2=[O:23])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 86629437HCID 86629437, compound

Product 1

HCID 67062977HCID 67062977, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution 3-(4-fluoro-3-nitrophenyl)-7-(methoxy(methyl)amino)-1-methyl-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (2 g, 5.5 mmol) in methanol (30 mL) was stirred with 10% Pd/C (1.0 g, 0.94 mmol) under hydrogen (45 psi) at 45° C. for 24 h. The complete reaction mixture was filtered, and the filtrate was concentrated in vacuo. The residue was washed with ethyl ether and dried in vacuo to provide 3-(3-amino-4-fluorophenyl)-1-methyl-7-(methylamino)-3,4-dihydropyrido[4,3-d]pyrimidin-2(1H)-one (1.1 g, 66% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.70 (s, 1 H), 6.94 (t, J=9.6 Hz, 1 H), 6.66 (d, J=6.8 Hz, 1 H), 6.40 (m, 2H), 5.92 (s, 1 H), 5.17 (s, 2 H), 4.50 (s, 2 H), 3.13 (s, 3 H), 2.73 (d, J=4.0 Hz, 3 H), MS (ESI) m/z: 302.1 (M+H+).

Workup

  1. filtrationThe complete reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. washThe residue was washed with ethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ab1d2aac69834d16a83552f274d27bb2
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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