N-(2-hydroxymethyl-5-nitro-phenyl)-4-(3-pyridinyl)-2-pyrimidinamine → N-(5-Amino-2-hydroxymethyl-phenyl)-4-(3-pyridinyl)-2-pyrimidinamine

HRID 225498Notes

Reaction equation

HRID 225498 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[NH:12][C:13]1[N:18]=[C:17]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:16]=[CH:15][N:14]=1.[H][H]>C(O)C.[Ni]>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[C:4]([NH:12][C:13]2[N:18]=[C:17]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH:16]=[CH:15][N:14]=2)[CH:5]=1

Participants

5

Reactant 2

HCID 68490828N-(2-hydroxymethyl-5-nitro-phenyl)-4-(3-pyridinyl)-2-pyrimidinamineHCID 178418361HCID 178418361, compound

Product 1

HCID 68493936N-(5-Amino-2-hydroxymethyl-phenyl)-4-(3-pyridinyl)-2-pyrimidinamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of N-(2-hydroxymethyl-5-nitro-phenyl)-4-(3-pyridinyl)-2-pyrimidinamine (0.23 g, 0.71 mmol) in ethanol (230 mL) is hydrogenated at atmospheric pressure over Raney nickel (0.2 g) at 25° C.. The calculated amount of hydrogen is taken up in 13 h. The mixture is then filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography on silica gel, eluent 25% aqueous ammonia-ethanol-dichloromethane (1:9:90), to give the title compound as a yellow crystalline solid, m.p. 213-215° C.

Workup

  1. filtrationThe mixture is then filtered
  2. customthe solvent is evaporated off under reduced pressure
  3. customto yield the crude product which
  4. customis purified by column chromatography on silica gel, eluent 25% aqueous ammonia-ethanol-dichloromethane (1:9:90)

Sources & evidence

ORD record
ord-91776da586934d3a8a6e31cae2aa16c8
Source dataset
uspto-grants-2009_07
Patent number
US07557105B2

Reaction notes

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