Tetrahydrofuran → [6-(5-Amino-2-methyl-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-(4-chloro-phenyl)amine

HRID 2092584Notes

Reaction equation

HRID 2092584 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[N:10]=[CH:11][C:12]3[CH2:18][N:17]([C:19]4[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:20]=4[CH3:28])[CH2:16][CH2:15][C:13]=3[N:14]=2)=[CH:4][CH:3]=1.C1COCC1>[Pd].CO>[NH2:25][C:23]1[CH:22]=[CH:21][C:20]([CH3:28])=[C:19]([N:17]2[CH2:16][CH2:15][C:13]3[N:14]=[C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:10]=[CH:11][C:12]=3[CH2:18]2)[CH:24]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 67327913(4-Chloro-phenyl)-[6-(2-methyl-5-nitro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]amine

Product 1

HCID 68253436[6-(5-Amino-2-methyl-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-(4-chloro-phenyl)amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (4-Chloro-phenyl)-[6-(2-methyl-5-nitro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]amine (100 mg, 0.25 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)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-yl]-(4-chloro-phenyl)amine [12]as a off white solid [Yield: 81.5 mg, 88.2%]

Workup

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

Sources & evidence

ORD record
ord-4b52154d081c449581fc4324cc050b5c
Source dataset
uspto-grants-2013_05
Patent number
US08440679B2

Reaction notes

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