2-Chloro-N-ethyl-5-nitro-4-pyrimidinamine → 2-Chloro-N4-ethyl-4,5-pyrimidinediamine

HRID 552111Notes

Reaction equation

HRID 552111 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5]([N+:11]([O-])=O)=[CH:4][N:3]=1.[H][H]>C1COCC1.[Ni]>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5]([NH2:11])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 71472332-Chloro-N-ethyl-5-nitro-4-pyrimidinamineHCID 178418361HCID 178418361, compound

Product 1

HCID 71471762-Chloro-N4-ethyl-4,5-pyrimidinediamineYield 92%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10.0 g (50 mmol, 1.0 eq.) of 2-chloro-N-ethyl-5-nitropyrimidin-4-amine (I-1) in 300 mL of THF was added ˜4.0 g of Raney Nickel. The solution was stirred under 1 atm. of hydrogen at room temperature for 12 h. The reaction mixture was filtered through Celite® and the pad was washed with 100 mL of THF. The solvent was removed in vacuo to provide 8.0 g (46 mmol, 92%) of 2-chloro-N4-ethylpyrimidine-4,5-diamine (I-5).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washthe pad was washed with 100 mL of THF
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-38388d12abce4ac490c2a8657fb2616a
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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