4-Morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-nitro-pyrido[2,3-d]pyrimidine → 4-Morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-amino-pyrido[2,3-d]pyrimidine

HRID 1879821Notes

Reaction equation

HRID 1879821 reaction equation
[N:1]1([C:7]2[C:8]3[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[N:22][C:9]=3[N:10]=[C:11]([O:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>CO.[Pd]>[N:1]1([C:7]2[C:8]3[CH:25]=[C:24]([NH2:26])[CH:23]=[N:22][C:9]=3[N:10]=[C:11]([O:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[N:12]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 689208664-Morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-nitro-pyrido[2,3-d]pyrimidine

Product 1

HCID 689245994-Morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-amino-pyrido[2,3-d]pyrimidineYield 46.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-nitro-pyrido[2,3-d]pyrimidine (3.35 g) was dissolved in methanol (100 mL), and to the solution was added 5% palladium on carbon (100 mg). The suspension was placed under an atmosphere of hydrogen, and stirred for five hours. The solution was filtered and evaporated, and then purified by column chromatography to give 4-morpholin-4-yl-2-(2-morpholin-4-yl-ethoxy)-6-amino-pyrido[2,3-d]pyrimidine (1.45 g) as a yellow oil.

Workup

  1. filtrationThe solution was filtered
  2. customevaporated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-5a8752da7b464fdaaf0a845ca1b27609
Source dataset
uspto-grants-2012_11
Patent number
US08318730B2

Reaction notes

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