HCID 58416768, compound → 4-((4-Aminonaphthalen-1-yloxy)methyl)pyrimidin-2-amine

HRID 2069072Notes

Reaction equation

HRID 2069072 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[N:17]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(Cl)Cl.CC(O)=O.[Pt]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH2:22])[N:17]=2)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 58416768HCID 58416768, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 584167554-((4-Aminonaphthalen-1-yloxy)methyl)pyrimidin-2-amineYield 91.1%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the nitroarene (70) (1.10 g, 3.71 mmol) in a mixture of DCM (50 mL) and AcOH (40 mL) was passed through a Thales H-cube (1.0 mL·min−1, 55 mm, 10% Pt/C, 40° C., full hydrogen mode). LC-MS analysis of the resulting solution showed a mixture comprising of mainly starting material and ca. 20% product. The DCM was removed by evaporation in vacuo and the solution re-subjected to reduction using the same conditions at RT. The volatiles were evaporated in vacuo to give the title compound (71) (ca. 70% by LC-MS) as a purple solid (0.90 g, 64% yield): m/z 267 (M+H)+ (ES+).

Workup

  1. customThe DCM was removed by evaporation in vacuo
  2. customat RT
  3. customThe volatiles were evaporated in vacuo

Sources & evidence

ORD record
ord-92c393a23d914fbaafe61733020b5b19
Source dataset
uspto-grants-2012_10
Patent number
US08299073B2

Reaction notes

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