Ammonium Chloride → 1-(2-fluorobenzyl)-8-(4-aminobenzyl)-3-butyl-1H-purine-2,6(3H,7H)-dione

HRID 858083Notes

Reaction equation

HRID 858083 reaction equation
[CH2:1]([N:5]1[C:10]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)=[CH:9][C:8](=[O:23])[N:7]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[C:6]1=[O:32])[CH2:2][CH2:3][CH3:4].[Cl-].[NH4+:34]>CO.O.[Zn]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:12]2[NH:34][C:9]3[C:8](=[O:23])[N:7]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[F:31])[C:6](=[O:32])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:10]=3[N:11]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 218918031-butyl-3-(2-fluorobenzyl)-6-[2-(4-nitro-phenyl)-ethylamino]-1H-pyrimidine-2,4-dione

Product 1

HCID 218917201-(2-fluorobenzyl)-8-(4-aminobenzyl)-3-butyl-1H-purine-2,6(3H,7H)-dioneYield 87.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-Butyl-3-(2-fluorobenzyl)-6-[2-(4-nitro-phenyl)-ethylamino]-1H-pyrimidine-2,4-dione (2.0 g, 4.46 mmol) was dissolved in methanol (100 mL) and treated with zinc dust (<10 μm, Aldrich; 2.91 g) followed by the addition of a solution of ammonium chloride (5.96 g, 112 mmol) in water (50 mL). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was then filtered through a pad of celite. The filtrate was concentrated to remove methanol and the residual aqueous solution was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo to afford 8-(4-amino-benzyl)-3-butyl-1-(2-fluorobenzyl)-3,7-dihydro-purine-2,6-dione as a pale yellow solid (1.64 g, 87%). LCMS, m/z(M+H)=422.18.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of celite
  2. concentrationThe filtrate was concentrated
  3. customto remove methanol
  4. extractionthe residual aqueous solution was extracted with ethyl acetate (3×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-10c53450241d419786dce2f1f31036b2
Source dataset
uspto-grants-2006_12
Patent number
US07148229B2

Reaction notes

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