Tetrahydrofuran → HCID 67328556, compound

HRID 2092589Notes

Reaction equation

HRID 2092589 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[N:17]=[CH:18][C:19]3[C:25](=[O:26])[N:24]([C:27]4[CH:32]=[C:31]([N+:33]([O-])=O)[CH:30]=[CH:29][C:28]=4[CH3:36])[CH2:23][CH2:22][C:20]=3[N:21]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1.C1COCC1>[Pd].CO>[NH2:33][C:31]1[CH:30]=[CH:29][C:28]([CH3:36])=[C:27]([N:24]2[CH2:23][CH2:22][C:20]3[N:21]=[C:16]([NH:15][C:4]4[CH:5]=[CH:6][C:7]([N:8]5[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]5)=[C:2]([CH3:1])[CH:3]=4)[N:17]=[CH:18][C:19]=3[C:25]2=[O:26])[CH:32]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 67329139HCID 67329139, compound

Product 1

HCID 67328556HCID 67328556, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[3-Methyl-4-(4-methyl-piperazin-1-yl)-phenylamino]-6-(2-methyl-5-nitro-phenyl)-7,8-dihydro-6H-pyrido[4,3-d]pyrimidin-5-one (100 mg, 0.198 mmol) in the mixed solvent of THF (5 ml) and methanol (5 ml) was added 10% Pd/C, and the reaction mixture was stirred for 12 hours at room temperature under a hydrogen balloon. The reaction mixture was filtered and the filtrate was concentrated under vacuum to give 6-(5-Amino-2-methyl-phenyl)-2-[3-methyl-4-(4-methyl-piperazin-1-yl)-phenylamino]-7,8-dihydro-6H-pyrido[4,3-d]pyrimidin-5-one [19] (Yield: 81.72 mg, 86.9%) as a off white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-8b111fec4256486bb9ac65546426f371
Source dataset
uspto-grants-2013_05
Patent number
US08440679B2

Reaction notes

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