Sulfuric Acid → HCID 86038807, compound

HRID 659999Notes

Reaction equation

HRID 659999 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[CH:21]=[C:20]([Cl:22])[N:19]=[CH:18][N:17]=2)=[CH:11][C:10]=1[N+:23]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C(O)C.[Zn]>[NH2:23][C:10]1[CH:11]=[C:12]([NH:15][C:16]2[CH:21]=[C:20]([Cl:22])[N:19]=[CH:18][N:17]=2)[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 86038803HCID 86038803, compound

Product 1

HCID 86038807HCID 86038807, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(4′-benzyloxy-3-nitrophenyl)amino-6-chloro-pyrimidine (4.91 g) and sulfuric acid (8 ml) in ethanol (300 ml) was added zinc dust (4.49 g). The mixture was then heated under reflux for 18 hours, cooled to room temperature then basified with sodium hydrogen carbonate. After evaporation under reduced pressure, the residue was dissolved in ethyl acetate and water. The organic phase was separated, washed with water, dried (MgSO4) and evaporated under reduced pressure. The residue was then subjected to column chromatography (SiO2; ethyl acetate:petroleum ether (40/60) 1:1) to give 4-(3′-amino-4′benzyloxyphenyl)amino-6-chloro-pyrimidine, 21% δH (d6 DMSO): 4.84 (2H, s, NH2), 5.00 (2H, s, CH2Ph), 6.50-6.60 (2H, m, ArH), 6.70-6.80 (2H, m, ArH and HetH), 7.20-7.50 (5H, m, ArH), 8.30 (1H, s, HetH), 9.45 (1H, s, NH)

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 18 hours
  3. customAfter evaporation under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. customThe organic phase was separated
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1327cc4a9dc14eba8d0e1994b5da7367
Source dataset
uspto-grants-2011_12
Patent number
US08084457B2

Reaction notes

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