Dichloromethane → 4-((4-Aminonaphthalen-1-yloxy)methyl)pyrimidin-2-amine

HRID 872418Notes

Reaction equation

HRID 872418 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.C(Cl)Cl.[H][H]>[Pt].CC(O)=O>[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 3

HCID 6344DichloromethaneHCID 58416768HCID 58416768, compoundHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4-((4-nitronaphthalen-1-yloxy)methyl)pyrimidin-2-amine (32) (1.10 g, 3.71 mmol) in a DCM (50 mL) and AcOH (40 mL) was passed through a Thales H-cube at 1.0 mL·min−1 (full hydrogen mode, 55 mm 10% Pt/C, 40° C.). LC-MS analysis of the solution showed mainly starting material and ca. 20% product. The DCM was evaporated and the solution re-subjected to the above reducing conditions at RT. Analysis showed ca. 70% product together with ca. 20% over reduction and ca. 10% starting material. The volatiles were evaporated to give crude 4-((4-aminonaphthalen-1-yloxy)methyl)pyrimidin-2-amine (33) as a purple solid (0.90 g, 64% yield): m/z 267 (M+H)+ (ES+).

Workup

  1. customThe DCM was evaporated
  2. customat RT
  3. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-3b227755dc55483a9fa53bbaca369886
Source dataset
uspto-grants-2015_03
Patent number
US08975285B2

Reaction notes

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